Aminoquinazoline Compounds for Combating Invertebrate Pests

ABSTRACT

The invention relates to aminoquinazoline compounds or the enantiomers or veterinarily acceptable salts thereof which are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes. The invention also relates to methods for controlling invertebrate pests by using these compounds and to plant propagation material and to agricultural and veterinary compositions comprising said compounds. 
     
       
         
         
             
             
         
       
     
     wherein A 1 , A 2 , A 3 , A 4 , R 1 , R 2 , R 3 , R 4 , R 5a , R 5b , R 5c , R 5d  and p are defined as in the description.

The present invention relates to aminoquinazoline compounds or theenantiomers or veterinarily acceptable salts thereof which are usefulfor combating or controlling invertebrate pests, in particular arthropodpests and nematodes. The invention also relates to methods forcontrolling invertebrate pests by using these compounds and to plantpropagation material and to agricultural and veterinary compositionscomprising said compounds.

Invertebrate pests and in particular arthropods and nematodes destroygrowing and harvested crops and attack wooden dwelling and commercialstructures, causing large economic loss to the food supply and toproperty. While a large number of pesticidal agents are known, due tothe ability of target pests to develop resistance to said agents, thereis an ongoing need for new agents for combating invertebrate pests, inparticular insects, arachnids and nematodes.

WO 2005/087742 describes quinoline derivatives usable as agents in thecontrol of pests for crop protection, human and animal health, acting asethanolamine kinase inhibitors.

EP-A-393999 describes quinazolinylsulfonylureidoazines useful asherbicides.

DE-A-19756388 describes substituted 2-aryl-4-amino-quinazolines andtheir use as cardiovascular agents for treatment of circulatorydiseases, blood pressure, angina, pectoris, heart insufficiency,thrombosis or artherosclorosis and to modulate the production of cGMP.

WO 2002/24667 describes 4-amino-quinazolines as glycoprotein IbIXantagonists.

WO 2004/030672 describes the use of 4-amino-quinazolines as anti canceragents and PKB inhibitors.

WO 2004/092196 describes among other quinazolines derivatives compoundsfor modulating protein kinase enzymatic activity.

It is an object of the present invention to provide compounds that havea good pesticidal activity, in particular insecticidal activity, andshow a broad activity spectrum against a large number of differentinvertebrate pests, especially against difficult to control arthropodpests and/or nematodes.

It has been found that these objectives can be achieved byaminoquinazoline compounds of the formula I below, by their steroisomersand by their salts and N-oxides, in particular their agriculturally orveterinarily acceptable salts.

Therefore, in a first aspect, the invention relates to aminoquinazolinecompounds of the formula I and the salts and N-oxides thereof

wherein

-   A¹, A², A³ and A⁴ are N, NX or CR⁴ wherein X is a lone pair or O,    with the proviso that at most three of A¹, A², A³ and A⁴ are N or    NX;-   R¹, R² are selected independently from one another from the group    consisting of hydrogen, CN, NO₂, C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl,    C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl,    -   wherein the carbon atoms of the aforementioned aliphatic and        cycloaliphatic radicals may be unsubstituted or substituted with        one or more R⁶⁻;    -   Si(R¹¹)₂R¹², OR⁷, S(O)_(m)R⁷, NR⁸R⁹, N═C(R⁶)₂, C(═O)R⁶, C(═S)R⁶,        C(═NR⁸)R⁶    -   and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,        -   wherein said heterocyclic ring        -   is saturated or partially saturated,        -   comprises 1, 2 or 3 heteroatoms selected from oxygen,            nitrogen and/or sulfur, wherein the nitrogen and/or the            sulfur atom(s) may be oxidized,        -   is unsubstituted or substituted with one to five R¹⁰, and        -   wherein one or two CH₂ groups in said heterocyclic ring may            be replaced by one or two C═O groups;-   R³ is selected from the group consisting of hydrogen, halogen,    cyano, azido, nitro, SCN, SF₅, C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl,    C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl,    -   wherein the carbon atoms of the aforementioned aliphatic and        cycloaliphatic radicals may be unsubstituted or substituted with        one or more R⁶;    -   Si(R¹¹)₂R¹², OR⁷, N(R⁸)R⁹, N═C(R⁶)₂, C(═O)R⁶, C(═S)R⁶,        C(═NR⁸)R⁶, phenyl        -   which may be substituted with 1, 2, 3, 4 or 5 radicals R¹⁰;    -   and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,        -   wherein said heterocyclic ring            -   is saturated or partially saturated,            -   comprises 1, 2 or 3 heteroatoms or heteroatom groups                selected from N, O, S, NO, SO and SO₂,            -   is unsubstituted or substituted with one to five                radicals R¹⁰, and            -   wherein one or two CH₂ groups in said heterocyclic ring                may be replaced by one or two C═O groups;-   each R⁴ is selected independently from the group consisting of    hydrogen, halogen, cyano, azido, nitro, SCN, SF₅, C₁-C₁₀ alkyl,    C₃-C₈-cycloalkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl,    -   wherein the carbon atoms of the aforementioned aliphatic and        cycloaliphatic radicals may be unsubstituted or substituted with        one or more R⁶;    -   Si(R¹¹)₂R¹², OR⁷, S(O)_(m)R⁷, N(R⁶)R⁹, N═C(R⁶)₂, C(═O)R⁶,        C(═S)R⁶, C(═NR⁸)R⁶, C(═O)N(R⁸)R⁹, C(═S)N(R⁸)R⁹, phenyl        -   which may be substituted with 1, 2, 3, 4 or 5 radicals R¹⁰;    -   and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,        -   wherein said heterocyclic ring            -   is saturated or partially unsaturated or aromatic,            -   comprises 1, 2 or 3 heteroatoms or heteroatom groups                selected from N, O, S, NO, SO and SO₂,            -   is unsubstituted or substituted with one to five                radicals R¹⁰, and wherein one or two CH₂ groups in said                saturated or partially saturated rings may be replaced                by one or two C═O groups;    -   or two radicals R⁴ bound on adjacent carbon atoms together form        a group selected from —CH₂CH₂CH₂CH₂—, —CH═CH—CH═CH—,        —N═CH—CH═CH—, —CH═N—CH═CH—, —N═CH—N═CH—, —OCH₂CH₂CH₂—,        —OCH═CHCH₂—, —CH₂OCH₂CH₂—, —OCH₂CH₂O—, —OCH₂OCH₂—, —CH₂CH₂CH₂—,        —CH═CHCH₂—, —CH₂CH₂O—, —CH═CHO—, —CH₂OCH₂—, —CH₂C(═O)O—,        —C(═O)OCH₂—, —O(CH₂)O—, —SCH₂CH₂CH₂—, —SCH═CHCH₂—, —CH₂SCH₂CH₂—,        —SCH₂CH₂S—, —SCH₂SCH₂—, —CH₂CH₂S—, —CH═CHS—, —CH₂SCH₂—,        —CH₂C(═S)S—, —C(═S)SCH₂—, —S(CH₂)S—, —CH₂CH₂NR⁸—, —CH₂CH═N—,        —CH═CH—NR⁸—, —OCH═N— and —SCH═N—,        -   wherein in each of the above group,        -   one to five hydrogen atoms independently of each other may            be replaced by one to five substituents selected from            halogen, methyl, halomethyl, hydroxyl, methoxy and            halomethoxy, or        -   one or two CH₂ groups of the above groups may be replaced by            one or two C═O groups;-   R^(5a) is selected from the group consisting of hydrogen, halogen,    cyano, azido, nitro, SCN, SF₅, C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl,    C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl,    -   wherein the carbon atoms of the aforementioned aliphatic and        cycloaliphatic radicals may be unsubstituted or substituted with        one or more R⁶;    -   Si(R¹¹)₂R¹², OR⁷, S(O)_(m)R⁷, N(R⁸)R⁹, N═C(R⁶)₂, C(═O)R⁶,        C(═S)R⁶, C(═NR⁸)R⁶, phenyl        -   which may be substituted with 1, 2, 3, 4 or 5 radicals R¹⁰;    -   and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,        -   wherein said heterocyclic ring        -   is saturated or partially unsaturated or aromatic,            -   comprises 1, 2 or 3 heteroatoms or heteroatom groups                selected from N, O, S, NO, SO and SO₂,            -   is unsubstituted or substituted with one to five                radicals R¹⁰, and            -   wherein one or two CH₂ groups in said saturated or                partially saturated rings may be replaced by one or two                C═O groups;    -   or R^(5a) may form together with the adjacent carbon atom R^(5b)        a 5- or 6-membered ring which is at least substituted with one        halogen;-   R^(5b) is selected from the group consisting of C₁-C₆-alkyl,    C₃-C₆-cycloalkyl, C₁-C₆-alkoxy and C₁-C₆-cycloalkoxy, wherein each    mentioned radical    -   is at least substituted with one halogen,    -   may be further partially or fully halogenated, and    -   may be substituted with one to five radicals R⁶;    -   or R^(5b) may form together with the adjacent carbon atom R^(5c)        or R^(5a) a 5- or 6-membered ring which is at least substituted        with one halogen;-   R^(5c) is selected from the group consisting of hydrogen, halogen,    cyano, azido, nitro, SCN, SF₅, C₃-C₈-cycloalkyl, C₂-C₁₀-alkenyl,    C₂-C₁₀-alkynyl,    -   wherein the carbon atoms of the aforementioned aliphatic and        cycloaliphatic radicals may be unsubstituted or substituted with        one or more R⁶;    -   Si(R¹¹)₂R¹², OR⁷, S(O)_(m)R⁷, N(R⁸)R⁹, N═C(R⁶)₂, C(═O)OR⁷,        C(═S)OR⁷, C(═NR⁸)R⁶, C(═O)N(R⁸)R⁹, C(═S)N(R⁸)R⁹, phenyl        -   which may be substituted with 1, 2, 3, 4 or 5 radicals R¹⁰;    -   and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,        -   wherein said heterocyclic ring        -   is saturated, partially unsaturated or aromatic,        -   comprises 1, 2 or 3 heteroatoms or heteroatom groups            selected from N, O, S, NO, SO and SO₂,        -   is unsubstituted or substituted with one to five radicals            R¹⁰, and        -   wherein one or two CH₂ groups in said saturated or partially            saturated rings may be replaced by one or two C═O groups;    -   or R^(5c) may form together with the adjacent carbon atom R^(5b)        or R^(5d) a 5- or 6-membered ring which is at least substituted        with one halogen in case of R^(5b) beings involved;-   R^(5d) is selected from the group consisting of hydrogen, halogen,    cyano, azido, nitro, SCN, SF₅, C₃-C₈-cycloalkyl, C₂-C₁₀-alkenyl,    C₂-C₁₀-alkynyl,    -   wherein the carbon atoms of the aforementioned aliphatic and        cycloaliphatic radicals may be unsubstituted or substituted with        one or more R⁶;    -   Si(R¹¹)₂R¹², OR⁷, S(O)_(m)N(R⁸)R⁹, N(R⁸)R⁹, N═C(R⁶)₂, C(═O)R⁶,        C(═S)R⁶, C(═NR⁸)R⁶, phenyl        -   which may be substituted with 1, 2, 3, 4 or 5 radicals R¹⁰;    -   and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,        -   wherein said heterocyclic ring            -   is saturated, partially unsaturated or aromatic,            -   comprises 1, 2 or 3 heteroatoms or heteroatom groups                selected from N, O, S, NO, SO and SO₂,            -   is unsubstituted or substituted with one to five                radicals R¹⁰, and            -   wherein one or two CH₂ groups in said saturated or                partially saturated rings may be replaced by one or two                C═O groups;    -   or R^(5d) may form together with the adjacent carbon atom R^(5c)        or with R¹ or R² a 5- or 6-membered ring;-   R⁶ is independently selected independently from the group consisting    of hydrogen, halogen, cyano, azido, nitro, SCN, SF₅, C₁-C₆-alkyl,    C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl,    C₁-C₆-alkylsulfonyl, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl,    C₂-C₆-alkenyl, C₂-C₆-alkynyl,    -   wherein the carbon atom of the aforementioned aliphatic and    -   cycloaliphatic radicals may be substituted with one or more        R^(c);    -   Si(R¹¹)₂R¹², OR^(o), O(CO)R^(c), O(CS)R^(c), S(O)_(m)R^(o),        S(O)_(m)N(R^(n))₂, S(CO)R^(c), S(CS)R^(c), S(C═NR^(n))R^(c),        N(R^(n))₂, N(R^(n))C(═O)R^(o), N(R^(n))C(═S)R^(c),        NS(O)_(m)R^(o), N═C(R^(c))₂, C(═O)R^(c), C(═S)R^(c),        C(═NR^(n))R^(o), C(═O)N(R^(n))₂, C(═S)N(R^(n))₂, phenyl        -   which may be substituted with 1, 2, 3, 4 or 5 radicals R¹⁰;    -   and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,        -   wherein said heterocyclic ring            -   is saturated, partially unsaturated or aromatic,            -   comprises 1, 2 or 3 heteroatoms or heteroatom groups                selected from N, O, S, NO, SO and SO₂,            -   is unsubstituted or substituted with one to five                radicals R¹⁰, and            -   wherein one or two CH₂ groups in said saturated or                partially saturated rings may be replaced by one or two                0=0 groups;    -   or two vicinally bound radicals R⁶ together form a group        selected from ═C(R^(c))₂, ═S(O)_(m)R^(o), ═S(O)_(m)N(R^(n))₂,        ═NR^(n) and ═NN(R^(n))₂;-   R⁷ is independently selected independently from the group consisting    of hydrogen, cyano, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio,    C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, C₃-C₈-cycloalkyl,    C₃-C₅-cycloalkyl-C₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,    -   wherein the carbon atom of the aforementioned aliphatic and    -   cycloaliphatic radicals may be substituted with one or more        R^(c);    -   Si(R¹¹)₂R¹², OR^(o), O(CO)R^(c), O(CS)R^(c), S(O)_(m)R^(o),        S(O)_(m)N(R^(n))₂, S(CO)R^(c), S(CS)R^(c), S(C═NR^(n))R^(c),        N(R^(n))₂, N(R^(n))C(═O)R^(c), N(R^(n))C(═S)R^(o),        NS(O)_(m)R^(c), N═C(R^(c))₂, C(═O)R^(c), C(═S)R^(c),        C(═NR^(n))R^(c), C(═O)N(R^(n))₂, C(═S)N(R^(n))₂, phenyl        -   which may be substituted with 1, 2, 3, 4 or 5 radicals R¹⁰;    -   and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,        -   wherein said heterocyclic ring            -   is saturated, partially unsaturated or aromatic,            -   comprises 1, 2 or 3 heteroatoms or heteroatom groups                selected from N, O, S, NO, SO and SO₂,            -   is unsubstituted or substituted with one to five                radicals R¹⁰, and            -   wherein one or two CH₂ groups in said saturated or                partially saturated rings may be replaced by one or two                C═O groups;                with the proviso that R⁷ is not C₁-C₆-alkoxy or                C₁-C₆-haloalkoxy if it is bound to an oxygen atom;-   R⁸, R⁹ are selected independently from one another and independently    of each occurrence from the group consisting of hydrogen, CN, NO₂,    C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl,    C₁-C₆-alkylsulfonyl, C₃-C₈-cycloalkyl, C₃-C₅-cycloalkyl-C₁-C₄-alkyl,    C₂-C₆-alkenyl, C₂-C₆-alkynyl,    -   wherein the carbon atom of the aforementioned aliphatic and    -   cycloaliphatic radicals may be substituted with one or more        R^(c);    -   Si(R¹¹)₂R¹², OR^(o), O(CO)R^(c), O(CS)R^(c), S(O)_(m)R^(o),        S(O)_(m)N(R^(n))₂, S(CO)R^(c), S(CS)R^(c), S(C═NR^(n))R^(c),        N(R^(n))₂, N(R^(n))C(═O)R^(c), N(R^(n))C(═S)R^(c),        NS(O)_(m)R^(c), N═C(R^(c))₂, C(═O)R^(c), C(═S)R^(c),        C(═NR^(n))R^(c), C(═O)N(R^(n))₂, C(═S)N(R^(n))₂ phenyl        -   which may be substituted with 1, 2, 3, 4 or 5 radicals R¹⁰;    -   and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,        -   wherein said heterocyclic ring            -   is saturated, partially unsaturated or aromatic,            -   comprises 1, 2 or 3 heteroatoms or heteroatom groups                selected from N, O, S, NO, SO and SO₂,            -   is unsubstituted or substituted with one to five                radicals R¹⁰, and            -   wherein one or two CH₂ groups in said saturated or                partially saturated rings may be replaced by one or two                C═O groups;-   R¹⁰ is independently selected independently from the group    consisting of halogen, cyano, azido, nitro, SCN, SF₅, C₁-C₆-alkyl,    C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl,    C₁-C₆-alkylsulfonyl, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl,    C₂-C₆-alkenyl, C₂-C₆-alkynyl,    -   wherein the carbon atom of the aforementioned aliphatic and    -   cycloaliphatic radicals may be substituted with one or more        R^(c);    -   Si(R¹¹)₂R¹², OR^(o), O(CO)R^(c), O(CS)R^(c), S(O)_(m)R^(o),        S(O)_(m)N(R^(c))₂, S(CO)R^(c), S(CS)R^(c), S(C═NR^(n))R^(c),        N(R^(n))₂, N(R^(n))C(═O)R^(c), N(R^(n))C(═S)R^(c),        NS(O)_(m)R^(o), N═C(R^(c))₂, C(═O)R^(c), C(═S)R^(c),        C(═NR^(n))R^(c), C(═O)N(R^(n))₂, C(═S)N(R^(n))₂, phenyl        -   which may be substituted with one to five radicals            independently selected independently from halogen, cyano,            nitro, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and            C₁-C₆-haloalkoxy;    -   and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,        -   wherein said heterocyclic ring            -   is saturated or unsaturated,            -   comprises 1, 2 or 3 heteroatoms or heteroatom groups                selected from N, O, S, NO, SO and SO₂,            -   is unsubstituted or substituted with one to five                radicals independently selected independently from                halogen, cyano, nitro, C₁-C₆-alkyl, C₁-C₆-haloalkyl,                C₁-C₆-alkoxy and C₁-C₆-haloalkoxy;    -   or two radicals R¹⁰ bound on adjacent atoms together form a        group selected from —CH₂CH₂CH₂CH₂—, —CH═CH—CH═CH—, —N═CH—CH═CH—,        —CH═N—CH═CH—, —N═CH—N═CH—, —OCH₂CH₂CH₂—, —OCH═CHCH₂—,        —CH₂OCH₂CH₂—, —OCH₂CH₂O—, —OCH₂OCH₂—, —CH₂CH₂CH₂—, —CH═CHCH₂—,        —CH₂CH₂O—, —CH═CHO—, —CH₂OCH₂—, —CH₂C(═O)O—, —C(═O)OCH₂—,        —O(CH₂)O—, —SCH₂CH₂CH₂—, —SCH═CHCH₂—, —CH₂SCH₂CH₂—, —SCH₂CH₂S—,        —SCH₂SCH₂—, —CH₂CH₂S—, —CH═CHS—, —CH₂SCH₂—, —CH₂C(═S)S—,        —C(═S)SCH₂—, —S(CH₂)S—, —CH₂CH₂NR⁸—, —CH₂CH═N—, —CH═CH—NR⁸—,        —OCH═N— and —SCH═N—,        -   wherein in each of the above groups,        -   one to five hydrogen atoms independently of each other may            be replaced by one to five substituents selected from            halogen, methyl, halomethyl, hydroxyl, methoxy and            halomethoxy, or        -   one or two or more CH₂ groups of the above groups may be            replaced by one or two C═O groups;-   R¹¹, R¹² are selected independently of each other and independently    of each occurrence from the group consisting of C₁-C₄-alkyl,    C₃-C₆-cycloalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl and benzyl;-   R^(c) is independently selected independently from the group    consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF₅,    C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,    C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl,    C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,    C₁-C₆-haloalkylsulfonyl, C₃-C₈-cycloalkyl,    C₃-C₈-cycloalkyl-C₁-C₄-alkyl, C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl,    C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, phenyl, and a    3-, 4-, 5-, 6- or 7-membered heterocyclic ring,    -   wherein said heterocyclic ring        -   is saturated, partially unsaturated or aromatic,        -   comprises 1, 2 or 3 heteroatoms or heteroatom groups            selected from CO, N, O, S, NO, SO and SO₂,        -   is unsubstituted or substituted with one to five radicals,            which are selected independently of each other from halogen,            cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and            C₁-C₄-haloalkoxy;-   R^(o) is independently selected independently from the group    consisting of hydrogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl,    C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,    C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl,    C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl,    C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,    C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, phenyl, and a 3-, 4-, 5-, 6- or    7-membered heterocyclic ring,    -   wherein said heterocyclic ring        -   is saturated, partially unsaturated or aromatic,        -   comprises 1, 2 or 3 heteroatoms or heteroatom groups            selected from CO, N, O, S, NO, SO and SO₂,        -   is unsubstituted or substituted with one to five radicals,            which are selected independently of each other from halogen,            cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and            C₁-C₄-haloalkoxy;            with the proviso that R^(o) is not C₁-C₆-alkoxy or            C₁-C₆-haloalkoxy if it is bound to an oxygen atom;-   R^(n) is independently selected independently from the group    consisting of hydrogen, CN, NO₂, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,    C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl,    C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl, C₃-C₈-cycloalkyl,    C₃-C₈-cycloalkyl-C₁-C₄-alkyl, C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl,    C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, phenyl, and a    3-, 4-, 5-, 6- or 7-membered saturated heterocyclic ring,    -   wherein said heterocyclic ring        -   is saturated, partially unsaturated or aromatic,        -   comprises 1, 2 or 3 heteroatoms or heteroatom groups            selected from CO, N, O, S, NO, SO and SO₂,        -   is unsubstituted or substituted with one to five radicals,            which are selected independently of each other from halogen,            cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and            C₁-C₄-haloalkoxy;-   m is independently 0, 1 or 2;-   p is 0, 1, 2, 3 or 4;-   or enantiomers or diastereoisomers thereof or their agriculturally    or veterinarily acceptable salts.

The present invention also provides a composition comprising at leastone compound of the formula I as defined herein and/or an agriculturallyacceptable salt thereof and at least one inert solid/liquid and/or solidcarrier

The present invention also provides an agricultural compositioncomprising at least one compound of the formula I as defined herein andat least one agriculturally acceptable liquid and/or solid carrier.

The present invention also provides a veterinary composition comprisingat least one compound of the formula I as defined herein and/or aveterinarily acceptable salt thereof and at least one liquid and/orsolid carrier.

The present invention also provides a method for controlling orcombating invertebrate pests attack or infestation which methodcomprises treating the pests, their food supply, their habitat or theirbreeding, ground or a cultivated plant, plant propagation materials(such as seed), soil, area, material or environment in which the pestsare growing or may grow, with a pesticidally effective amount of atleast one compound of formula I or salt thereof as defined herein.

The present invention also relates to plant propagation material, inparticular to seed, comprising at least one compound of formula I or ancomposition comprising at least one compound of formula I or anagriculturally acceptable salt thereof as defined herein.

The present invention further relates to a method for treating orprotecting an animal from infestation or infection by parasites whichcomprises bringing the animal in contact with a parasiticidallyeffective amount of a compound of the formula I or a veterinarilyacceptable salt thereof as defined herein. Bringing the animal incontact with the compound I, its salt or the veterinary composition ofthe invention means applying or administering it to the animal.

If used, the term “steroisomers” encompasses both optical isomers, suchas enantiomers or diastereomers, the latter existing due to more thanone center of chirality in the molecule, as well as geometrical isomers(cis/trans isomers).

Depending on the substitution pattern, the compounds of the formula Imay have one or more centers of chirality, in which case they arepresent as mixtures of enantiomers or diastereomers. The inventionprovides both the pure enantiomers or diastereomers and their mixturesand the use according to the invention of the pure enantiomers ordiastereomers of the compound I or its mixtures. Suitable compounds ofthe formula I also include all possible geometrical stereoisomers(cis/trans isomers) and mixtures thereof. Cis/trans isomers may bepresent with respect to an imine group.

The compounds of the present invention may be amorphous or may exist inone or more different crystalline states (polymorphs) which may have adifferent macroscopic properties such as stability or show differentbiological properties such as activities. The present invention includesboth amorphous and crystalline compounds of the formula I, mixtures ofdifferent crystalline states of the respective compound I, as well asamorphous or crystalline salts thereof.

Salts of the compounds of the formula I are preferably agriculturallyand veterinarily acceptable salts. They can be formed in a customarymethod, e.g. by reacting the compound with an acid of the anion inquestion if the compound of formula I has a basic functionality or byreacting an acidic compound of formula I with a suitable base.

Suitable agriculturally acceptable salts are especially the salts ofthose cations or the acid addition salts of those acids whose cationsand anions, respectively, do not have any adverse effect on the actionof the compounds according to the present invention. Suitable cationsare in particular the ions of the alkali metals, preferably lithium,sodium and potassium, of the alkaline earth metals, preferably calcium,magnesium and barium, and of the transition metals, preferablymanganese, copper, zinc and iron, and also ammonium (NH⁴⁺) andsubstituted ammonium in which one to four of the hydrogen atoms arereplaced by C₁-C₄-alkyl, C₁-C₄-hydroxyalkyl, C₁-C₄-alkoxy,C₁-C₄-alkoxy-C₁-C₄-alkyl, hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl orbenzyl. Examples of substituted ammonium ions comprise methylammonium,isopropylammonium, dimethylammonium, diisopropylammonium,trimethylammonium, tetramethylammonium, tetraethylammonium,tetrabutylammonium, 2-hydroxyethylammonium,2-(2-hydroxyethoxy)ethylammonium, bis(2-hydroxyethyl)ammonium,benzyltrimethylammonium and benzyl-triethylammonium, furthermorephosphonium ions, sulfonium ions, preferably tri(C₁-C₄-alkyl)sulfonium,and sulfoxonium ions, preferably tri(C₁-C₄-alkyl)sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide,fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogenphosphate, phosphate, nitrate, hydrogen carbonate, carbonate,hexafluorosilicate, hexafluorophosphate, benzoate, and the anions ofC₁-C₄-alkanoic acids, preferably formate, acetate, propionate andbutyrate. They can be formed by reacting a compound of formula I with anacid of the corresponding anion, preferably of hydrochloric acid,hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

By the term “veterinarily acceptable salts” is meant salts of thosecations or anions which are known and accepted in the art for theformation of salts for veterinary use. Suitable acid addition salts,e.g. formed by compounds of formula I containing a basic nitrogen atom,e.g. an amino group, include salts with inorganic acids, for examplehydrochlorids, sulphates, phosphates, and nitrates and salts of organicacids for example acetic acid, maleic acid, dimaleic acid, fumaric acid,difumaric acid, methane sulfenic acid, methane sulfonic acid, andsuccinic acid.

The term “invertebrate pest” as used herein encompasses animalpopulations, such as insects, arachnids and nematodes, which may attackplants, thereby causing substantial damage to the plants attacked, aswell as ectoparasites which may infest animals, in particular warmblooded animals such as e.g. mammals or birds, or other higher animalssuch as reptiles, amphibians or fish, thereby causing substantial damageto the animals infested.

The term “plant propagation material” as used herein includes all thegenerative parts of the plant such as seeds and vegetative plantmaterial such as cuttings and tubers (e.g. potatoes), which can be usedfor the multiplication of the plant. This includes seeds, roots, fruits,tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants.Seedlings and young plants, which are to be transplanted aftergermination or after emergence from soil, may also be included. Theseplant propagation materials may be treated prophylactically with a plantprotection compound either at or before planting or transplanting.

The term “plants” comprises any types of plants including“non-cultivated plants” and in particular “cultivated plants”.

The term “non-cultivated plants” refers to any wild type species orrelated species or related genera of a cultivated plant.

The term “cultivated plants” as used herein includes plants which havebeen modified by breeding, mutagenesis or genetic engineering.Genetically modified plants are plants, which genetic material has beenso modified by the use of recombinant DNA techniques that under naturalcircumstances cannot readily be obtained by cross breeding, mutations ornatural recombination. Typically, one or more genes have been integratedinto the genetic material of a genetically modified plant in order toimprove certain properties of the plant. Such genetic modifications alsoinclude but are not limited to targeted post-transitional modificationof protein(s) (oligo- or polypeptides) poly for example by glycosylationor polymer additions such as prenylated, acetylated or farnesylatedmoieties or PEG moieties (e.g. as disclosed in Biotechnol Prog. 2001July-August; 17(4):720-8, Protein Eng Des Sel. 2004 January;17(1):57-66, Nat. Protoc. 2007; 2(5):1225-35, Curr. Opin. Chem. Biol.2006 October; 10(5):487-91. Epub 2006 August 28, Biomaterials. 2001March; 22(5):405-17, Bioconjug Chem. 2005 January-Feb.; 16(1):113-21).

The term “cultivated plants” as used herein further includes plants thathave been rendered tolerant to applications of specific classes ofherbicides, such as hydroxy-phenylpyruvate dioxygenase (HPPD)inhibitors; acetolactate synthase (ALS) inhibitors, such as sulfonylureas (see e.g. U.S. Pat. No. 6,222,100, WO 01/82685, WO 00/26390, WO97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO03/14357, WO 03/13225, WO 03/14356, WO 04/16073) or imidazolinones (seee.g. U.S. Pat. No. 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO03/13225, WO 03/14356, WO 04/16073); enolpyruvylshikimate-3-phosphatesynthase (EPSPS) inhibitors, such as glyphosate (see e.g. WO 92/00377);glutamine synthetase (GS) inhibitors, such as glufosinate (see e.g.EP-A-0242236, EP-A-242246) or oxynil herbicides (see e.g. U.S. Pat. No.5,559,024) as a result of conventional methods of breeding or geneticengineering. Several cultivated plants have been rendered tolerant toherbicides by conventional methods of breeding (mutagenesis), forexample Clearfield® summer rape (Canola) being tolerant toimidazolinones, e.g. imazamox. Genetic engineering methods have beenused to render cultivated plants, such as soybean, cotton, corn, beetsand rape, tolerant to herbicides, such as glyphosate and glufosinate,some of which are commercially available under the trade namesRoundupReady® (glyphosate) and LibertyLink® (glufosinate).

The term “cultivated plants” as used herein further includes plants thatare by the use of recombinant DNA techniques capable to synthesize oneor more insecticidal proteins, especially those known from the bacterialgenus bacillus, particularly from bacillus thuringiensis, such asä-endotoxins, e.g. CryIA(b), CryIA(c), CryIF, CryIF(a2), CryIIA(b),CryIIIA, CryIIIB(b1) or Cry9c; vegetative insecticidal proteins (VIP),e.g. VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins of bacteriacolonizing nematodes, for example Photorhabdus spp. or Xenorhabdus spp.;toxins produced by animals, such as scorpion toxins, arachnid toxins,wasp toxins, or other insect-specific neurotoxins; toxins produced byfungi, such Streptomycetes toxins, plant lectins, such as pea or barleylectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors,serine protease inhibitors, patatin, cystatin or papain inhibitors;ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin,luffin, saporin or bryodin; steroid metabolism enzymes, such as3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase,cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ionchannel blockers, such as blockers of sodium or calcium channels;juvenile hormone esterase; diuretic hormone receptors (helicokininreceptors); stilben synthase, bibenzyl synthase, chitinases orglucanases. In the context of the present invention these insecticidalproteins or toxins are to be understood expressly also as pre-toxins,hybrid proteins, truncated or otherwise modified proteins. Hybridproteins are characterized by a new combination of protein domains,(see, for example WO 02/015701). Further examples of such toxins orgenetically modified plants capable of synthesizing such toxins aredisclosed, for example, in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A427 529, EP-A 451 878, WO 03/018810 and WO 03/052073. These insecticidalproteins contained in the genetically modified plants impart to theplants producing these proteins protection from harmful pests fromcertain taxonomic groups of arthropods insects, particularly to beetles(Coleoptera), flies (Diptera), and butterflies and moths (Lepidoptera)and to plant parasitic nematodes (Nematoda).

The term “cultivated plants” as used herein further includes plants thatare by the use of recombinant DNA techniques capable to synthesize oneor more proteins to increase the resistance or tolerance of those plantsto bacterial, viral or fungal pathogens. Examples of such proteins arethe so-called “pathogenesis-related proteins” (PR proteins, see, forexample EP-A 0 392 225), plant disease resistance genes (for examplepotato cultivars, which express resistance genes acting againstPhytophthora infestans derived from the mexican wild potato Solanumbulbocastanum) or T4-lyso-zym (e.g. potato cultivars capable ofsynthesizing these proteins with increased resistance against bacteriasuch as Erwinia amylvora).

The term “cultivated plants” as used herein further includes plants thatare by the use of recombinant DNA techniques capable to synthesize oneor more proteins to increase the productivity (e.g. bio mass production,grain yield, starch content, oil content or protein content), toleranceto drought, salinity or other growth limiting environ-mental factors ortolerance to pests and fungal, bacterial or viral pathogens of thoseplants.

The term “cultivated plants” as used herein further includes plants thatcontain by the use of recombinant DNA techniques a modified amount ofsubstances of content or new substances of content, specifically toimprove human or animal nutrition, for example oil crops that producehealth-promoting long-chain omega-3 fatty acids or unsaturated omega-9fatty acids (e.g. Nexera® rape).

The term “cultivated plants” as used herein further includes plants thatcontain by the use of recombinant DNA techniques a modified amount ofsubstances of content or new substances of content, specifically toimprove raw material production, for example potatoes that produceincreased amounts of amylopectin (e.g. Amflora® potato).

The organic moieties mentioned in the above definitions of the variablesare—like the term halogen—collective terms for individual listings ofthe individual group members. The prefix C_(n)-C_(m) indicates in eachcase the possible number of carbon atoms in the group.

The term halogen denotes in each case fluorine, bromine, chlorine oriodine, in particular fluorine, chlorine or bromine.

The term “C₁-C₁₀-alkyl” as used herein and in the alkyl moieties ofalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl,alkoxycarbonyl and the like refers to saturated straight-chain orbranched hydrocarbon radicals having 1 to 2 (“C₁-C₂-alkyl”), 1 to 4(“C₁-C₄-alkyl”), 1 to 6 (“C₁-C₆-alkyl”), 1 to 8 (“C₁-C₈-alkyl”) or 1 to10 (“C₁-C₁₀-alkyl”) carbon atoms. C₁-C₂-alkyl is methyl or ethyl.C₁-C₄-alkyl is additionally propyl, isopropyl, butyl, 1-methylpropyl(sec-butyl), 2-methylpropyl (isobutyl) or 1,1-dimethylethyl(tert-butyl). C₁-C₆-alkyl is additionally also, for example, pentyl,1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl,1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, hexyl,1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl,1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl,2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl,1-ethyl-1-methylpropyl, or 1-ethyl-2-methylpropyl. C₁-C₈-alkyl isadditionally also, for example, heptyl, octyl, 2-ethylhexyl andpositional isomers thereof. C₁-C₁₀-alkyl is additionally also, forexample, nonyl, decyl and positional isomers thereof.

The term “C₁-C₁₀-haloalkyl” as used herein, which is also expressed as“C₁-C₁₀-alkyl which is partially or fully halogenated”, refers tostraight-chain or branched alkyl groups having 1 to 2(“C₁-C₂-haloalkyl”), 1 to 4 (“C₁-C₄-haloalkyl”), 1 to 6(“C₁-C₆-haloalkyl”), 1 to 8 (“C₁-C₈-haloalkyl”) or 1 to 10(“C₁-C₁₀-haloalkyl”) carbon atoms (as mentioned above), where some orall of the hydrogen atoms in these groups are replaced by halogen atomsas mentioned above: in particular C₁-C₂-haloalkyl, such as chloromethyl,bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl,difluoromethyl, trifluoromethyl, chlorofluoromethyl,dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl,1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl,2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl or1,1,1-trifluoroprop-2-yl.

“Halomethyl” is methyl in which 1, 2 or 3 of the hydrogen atoms arereplaced by halogen atoms. Examples are bromomethyl, chloromethyl,fluoromethyl, dichloromethyl, trichloromethyl, difluoromethyl,trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl,chlorodifluoromethyl and the like.

The term “C₂-C₁₀-alkenyl” as used herein and in the alkenyl moiety ofalkenyloxy and the like refers to monounsaturated straight-chain orbranched hydrocarbon radicals having 2 to 4 (“C₂-C₄-alkenyl”), 2 to 6(“C₂-C₆-alkenyl”), 2 to 8 (“C₂-C₈-alkenyl”), 3 to 8 (“C₃-C₈-alkenyl”), 2to 10 (“C₂-C₁₀-alkenyl”) or 3 to 10 (“C₃-C₁₀-alkenyl”) carbon atoms anda double bond in any position, for example C₂-C₄-alkenyl, such asethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl,3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenylor 2-methyl-2-propenyl; C₂-C₆-alkenyl, such as ethenyl, 1-propenyl,2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl,1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl,2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl,1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl,1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl,1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl,1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl,1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl,1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl,1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl,4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl,3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl,2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl,1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl,4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl,1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl,1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl,2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl,2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl,1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl,2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl,1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl,1-ethyl-2-methyl-1-propenyl, 1-ethyl-2-methyl-2-propenyl and the like,or C₂-C₁₀-alkenyl, such as the radicals mentioned for C₂-C₆-alkenyl andadditionally 1-heptenyl, 2-heptenyl, 3-heptenyl, 1-octenyl, 2-octenyl,3-octenyl, 4-octenyl, 1-nonenyl, 2-nonenyl, 3-nonenyl, 4-nonenyl,1-decenyl, 2-decenyl, 3-decenyl, 4-decenyl, 5-decenyl and the positionalisomers thereof.

The term “C₂-C₁₀-haloalkenyl” as used herein, which is also expressed as“C₁-C₁₀-alkenyl which is partially or fully halogenated”, and thehaloalkenyl moieties in haloalkenyloxy, haloalkenylcarbonyl and the likerefers to unsaturated straight-chain or branched hydrocarbon radicalshaving 2 to 4 (“C₂-C₄-haloalkenyl”), 2 to 6 (“C₂-C₆-haloalkenyl”), 2 to8 (“C₂-C₆-haloalkenyl”) or 2 to 10 (“C₂-C₁₀-haloalkenyl”) carbon atomsand a double bond in any position (as mentioned above), where some orall of the hydrogen atoms in these groups are replaced by halogen atomsas mentioned above, in particular fluorine, chlorine and bromine, forexample chlorovinyl, chloroallyl and the like.

The term “C₂-C₁₀-alkynyl” as used herein and the alkynyl moieties inalkynyloxy, alkynylcarbonyl and the like refers to straight-chain orbranched hydrocarbon groups having 2 to 4 (“C₂-C₄-alkynyl”), 2 to 6(“C₂-C₆-alkynyl”), 2 to 8 (“C₂-C₈-alkynyl”), 3 to 8 (“C₃-C₈-alkynyl”), 2to 10 (“C₂-C₁₀-alkynyl”) or 3 to 10 (“C₃-C₈-alkynyl”) carbon atoms andone or two triple bonds in any position, for example C₂-C₄-alkynyl, suchas ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl,1-methyl-2-propynyl and the like, C₂-C₆-alkynyl, such as ethynyl,1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl,1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl,1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl,3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl,1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl,1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl,2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl,3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl,1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl,2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl,1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl andthe like;

The term “C₂-C₁₀-haloalkynyl” as used herein, which is also expressed as“C₁-C₁₀-alkynyl which is partially or fully halogenated”, and thehaloalkynyl moieties in haloalkynyloxy, haloalkynylcarbonyl and the likerefers to unsaturated straight-chain or branched hydrocarbon radicalshaving 2 to 4 (“C₂-C₄-haloalkynyl”), 3 to 4 (“C₃-C₄-haloalkynyl”), 2 to6 (“C₂-C₆-haloalkynyl”), 3 to 6 (“C₃-C₆-haloalkynyl”), 2 to 8(“C₂-C₈-haloalkynyl”), 3 to 8 (“C₃-C₈-haloalkynyl”), 2 to 10(“C₂-C₁₀-haloalkynyl”) or 3 to 10 (“C₃-C₁₀-haloalkynyl”)carbon atoms andone or two triple bonds in any position (as mentioned above), where someor all of the hydrogen atoms in these groups are replaced by halogenatoms as mentioned above, in particular fluorine, chlorine and bromine;

The term “C₃-C₈-cycloalkyl” as used herein refers to mono- or bi- orpolycyclic saturated hydrocarbon radicals having 3 to 8, in particular 3to 6 carbon atoms (“C₃-C₆-cycloalkyl”). Examples of monocyclic radicalshaving 3 to 6 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyland cyclohexyl. Examples of monocyclic radicals having 3 to 8 carbonatoms comprise cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,cycloheptyl and cyclooctyl. Examples of bicyclic radicals having 7 or 8carbon atoms comprise bicyclo[2.2.1]heptyl, bicyclo[3.1.1]heptyl,bicyclo[2.2.2]octyl and bicyclo[3.2.1]octyl.

The term “C₃-C₈-halocycloalkyl” as used herein, which is also expressedas “C₃-C₈-cycloalkyl which is partially or fully halogenated”, and thehalocycloalkyl moieties in halocycloalkoxy, halocycloalkylcarbonyl andthe like refers to mono- or bi- or polycyclic saturated hydrocarbongroups having 3 to 8 (“C₃-C₃-halocycloalkyl”) or preferably 3 to 6(“C₃-C₆-halocycloalkyl”) carbon ring members (as mentioned above) inwhich some or all of the hydrogen atoms are replaced by halogen atoms asmentioned above, in particular fluorine, chlorine and bromine.

The term “C₃-C₈-cycloalkyl-C₁-C₄-alkyl” refers to a C₃-C₈-cycloalkylgroup as defined above which is bound to the remainder of the moleculevia a C₁-C₄-alkyl group, as defined above. Examples arecyclopropylmethyl, cyclopropylethyl, cyclopropylpropyl,cyclobutylmethyl, cyclobutylethyl, cyclobutylpropyl, cyclopentylmethyl,cycloppentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl,cyclohexylpropyl, and the like.

The term “C₁-C₂-alkoxy” is a C₁-C₂-alkyl group, as defined above,attached via an oxygen atom. The term “C₁-C₄-alkoxy” is a C₁-C₄-alkylgroup, as defined above, attached via an oxygen atom. The term“C₁-C₆-alkoxy” is a C₁-C₆-alkyl group, as defined above, attached via anoxygen atom. The term “C₁-C₁₀-alkoxy” is a C₁-C₁₀-alkyl group, asdefined above, attached via an oxygen atom. C₁-C₂-alkoxy is methoxy orethoxy. C₁-C₄-alkoxy is additionally, for example, n-propoxy,1-methylethoxy (isopropoxy), butoxy, 1-methylpropoxy (sec-butoxy),2-methylpropoxy (isobutoxy) or 1,1-dimethylethoxy (tert-butoxy).C₁-C₆-alkoxy is additionally, for example, pentoxy, 1-methylbutoxy,2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy,1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy,1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy,1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy,2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy,1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy,1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or1-ethyl-2-methylpropoxy. C₁-C₈-alkoxy is additionally, for example,heptyloxy, octyloxy, 2-ethylhexyloxy and positional isomers thereof.C₁-C₁₀-alkoxy is additionally, for example, nonyloxy, decyloxy andpositional isomers thereof.

The term “C₁-C₂-haloalkoxy” is a C₁-C₂-haloalkyl group, as definedabove, attached via an oxygen atom. The term “C₁-C₄-haloalkoxyl” is aC₁-C₄-haloalkyl group, as defined above, attached via an oxygen atom.The term “C₁-C₆-haloalkoxy” is a C₁-C₆-haloalkyl group, as definedabove, attached via an oxygen atom. The term “C₁-C₁₀-haloalkoxy” is aC₁-C₁₀-haloalkyl group, as defined above, attached via an oxygen atom.C₁-C₂-Haloalkoxy is, for example, OCH₂F, OCHF₂, OCF₃, OCH₂Cl, OCHCl₂,OCCl₃, chlorofluoromethoxy, dichlorofluoromethoxy,chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy,2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy,2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy,2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy or OC₂F₅.C₁-C₄-Haloalkoxy is additionally, for example, 2-fluoropropoxy,3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy,2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy,3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy,OCH₂—C₂F₅, OCF₂—C₂F₅, 1-(CH₂F)-2-fluoroethoxy, 1-(CH₂Cl)-2-chloroethoxy,1-(CH₂Br)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxyor nonafluorobutoxy. C₁-C₆-Haloalkoxy is additionally, for example,5-fluoropentoxy, 5-chloropentoxy, 5-brompentoxy, 5-iodopentoxy,undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy,6-iodohexoxy or dodecafluorohexoxy.

The term “C₁-C₂-alkylthio” is a C₁-C₂-alkyl group, as defined above,attached via a sulfur atom. The term “C₁-C₄-alkylthio” is a C₁-C₄-alkylgroup, as defined above, attached via a sulfur atom. The term“C₁-C₆-alkylthio” is a C₁-C₆-alkyl group, as defined above, attached viaa sulfur atom. The term “C₁-C₁₀-alkylthio” is a C₁-C₁₀-alkyl group, asdefined above, attached via a sulfur atom. C₁-C₂-alkylthio is methylthioor ethylthio. C₁-C₄-alkylthio is additionally, for example,n-propylthio, 1-methylethylthio (isopropylthio), butylthio,1-methylpropylthio (sec-butylthio), 2-methylpropylthio (isobutylthio) or1,1-dimethylethylthio (tert-butylthio). C₁-C₆-alkylthio is additionally,for example, pentylthio, 1-methylbutylthio, 2-methylbutylthio,3-methylbutylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio,2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio,1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio,4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio,1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio,3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio,1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio,1-ethyl-1-methylpropylthio or 1-ethyl-2-methylpropylthio.C₁-C₈-alkylthio is additionally, for example, heptylthio, octylthio,2-ethylhexylthio and positional isomers thereof. C₁-C₁₀-alkylthio isadditionally, for example, nonylthio, decylthio and positional isomersthereof.

The term “C₁-C₂-haloalkylthio” is a C₁-C₂-haloalkyl group, as definedabove, attached via a sulfur atom. The term “C₁-C₄-haloalkylthio” is aC₁-C₄-haloalkyl group, as defined above, attached via a sulfur atom. Theterm “C₁-C₆-haloalkylthio” is a C₁-C₆-haloalkyl group, as defined above,attached via a sulfur atom. The term “C₁-C₁₀-haloalkylthio” is aC₁-C₁₀-haloalkyl group, as defined above, attached via a sulfur atom.C₁-C₂-haloalkylthio is, for example, SCH₂F, SCHF₂, SCF₃, SCH₂Cl, SCHCl₂,SCCl₃, chlorofluoromethylthio, dichlorofluoromethylthio,chlorodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio,2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio,2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio,2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio,2,2,2-trichloroethylthio or SC₂F₅. C₁-C₄-Haloalkylthio is additionally,for example, 2-fluoropropylthio, 3-fluoropropylthio,2,2-difluoropropylthio, 2,3-difluoropropylthio, 2-chloropropylthio,3-chloropropylthio, 2,3-dichloropropylthio, 2-bromopropylthio,3-bromopropylthio, 3,3,3-trifluoropropylthio, 3,3,3-trichloropropylthio,SCH₂—C₂F₅, SCF₂—C₂F₅, 1-(CH₂F)-2-fluoroethylthio,1-(CH₂Cl)-2-chloroethylthio, 1-(CH₂Br)-2-bromoethylthio,4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio ornonafluorobutylthio. C₁-C₆-Haloalkylthio is additionally, for example,5-fluoropentylthio, 5-chloropentylthio, 5-brompentylthio,5-iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio,6-chlorohexylthio, 6-bromohexylthio, iodohexylthio ordodecafluorohexylthio.

The term “C₁-C₂-alkylsulfinyl” is a C₁-C₂-alkyl group, as defined above,attached via a sulfinyl [S(O)] group. The term “C₁-C₄-alkylsulfinyl” isa C₁-C₄-alkyl group, as defined above, attached via a sulfinyl [S(O)]group. The term “C₁-C₆-alkylsulfinyl” is a C₁-C₆-alkyl group, as definedabove, attached via a sulfinyl [S(O)] group. The term“C₁-C₁₀-alkylsulfinyl” is a C₁-C₁₀-alkyl group, as defined above,attached via a sulfinyl [S(O)] group. C₁-C₂-Alkylsulfinyl ismethylsulfinyl or ethylsulfinyl. C₁-C₄-Alkylsulfinyl is additionally,for example, n-propylsulfinyl, 1-methylethylsulfinyl(isopropylsulfinyl), butylsulfinyl, 1-methylpropylsulfinyl(sec-butylsulfinyl), 2-methylpropylsulfinyl (isobutylsulfinyl) or1,1-dimethylethylsulfinyl (tert-butylsulfinyl). C₁-C₆-Alkylsulfinyl isadditionally, for example, pentylsulfinyl, 1-methylbutylsulfinyl,2-methylbutylsulfinyl, 3-methylbutylsulfinyl,1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl,2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, hexylsulfinyl,1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl,4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl,1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl,2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl,3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl,1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl,1-ethyl-1-methylpropylsulfinyl or 1-ethyl-2-methylpropylsulfinyl.C₁-C₈-Alkylsulfinyl is additionally, for example, heptylsulfinyl,octylsulfinyl, 2-ethylhexylsulfinyl and positional isomers thereof.C₁-C₁₀-Alkylsulfinyl is additionally, for example, nonylsulfinyl,decylsulfinyl and positional isomers thereof.

The term “C₁-C₂-haloalkylsulfinyl” is a C₁-C₂-haloalkyl group, asdefined above, attached via a sulfinyl [S(O)] group. The term“C₁-C₄-haloalkylsulfinyl” is a C₁-C₄-haloalkyl group, as defined above,attached via a sulfinyl [S(O)] group. The term “C₁-C₆-haloalkylsulfinyl”is a C₁-C₆-haloalkyl group, as defined above, attached via a sulfinyl[S(O)] group. The term “C₁-C₁₀-haloalkylsulfinyl” is a C₁-C₁₀-haloalkylgroup, as defined above, attached via a sulfinyl [S(O)] group.C₁-C₂-Haloalkylsulfinyl is, for example, S(O)CH₂F, S(O)CHF₂, S(O)CF₃,S(O)CH₂Cl, S(O)CHCl₂, S(O)CCl₃, chlorofluoromethylsulfinyl,dichlorofluoromethylsulfinyl, chlorodifluoromethylsulfinyl,2-fluoroethylsulfinyl, 2-chloroethylsulfinyl, 2-bromoethylsulfinyl,2-iodoethylsulfinyl, 2,2-difluoroethylsulfinyl,2,2,2-trifluoroethylsulfinyl, 2-chloro-2-fluoroethylsulfinyl,2-chloro-2,2-difluoroethylsulfinyl, 2,2-dichloro-2-fluoroethylsulfinyl,2,2,2-trichloroethylsulfinyl or S(O)C₂F₅. C₁-C₄-Haloalkylsulfinyl isadditionally, for example, 2-fluoropropylsulfinyl,3-fluoropropylsulfinyl, 2,2-difluoropropylsulfinyl,2,3-difluoropropylsulfinyl, 2-chloropropylsulfinyl,3-chloropropylsulfinyl, 2,3-dichloropropylsulfinyl,2-bromopropylsulfinyl, 3-brornopropylsulfinyl,3,3,3-trifluoropropylsulfinyl, 3,3,3-trichloropropylsulfinyl,S(O)CH₂—C₂F₅, S(O)CF₂—C₂F₅, 1-(CH₂F)-2-fluoroethylsulfinyl,1-(CH₂Cl)-2-chloroethylsulfinyl, 1-(CH₂Br)-2-bromoethylsulfinyl,4-fluorobutylsulfinyl, 4-chlorobutylsulfinyl, 4-bromobutylsulfinyl ornonafluorobutylsulfinyl. C₁-C₆-Haloalkylsulfinyl is additionally, forexample, 5-fluoropentylsulfinyl, 5-chloropentylsulfinyl,5-brompentylsulfinyl, 5-iodopentylsulfinyl, undecafluoropentylsulfinyl,6-fluorohexylsulfinyl, 6-chlorohexylsulfinyl, 6-bromohexylsulfinyl,6-iodohexylsulfinyl or dodecafluorohexylsulfinyl.

The term “C₁-C₂-alkylsulfonyl” is a C₁-C₂-alkyl group, as defined above,attached via a sulfonyl [S(O)₂] group. The term “C₁-C₄-alkylsulfonyl” isa C₁-C₄-alkyl group, as defined above, attached via a sulfonyl [S(O)₂]group. The term “C₁-C₆-alkylsulfonyl” is a C₁-C₆-alkyl group, as definedabove, attached via a sulfonyl [S(O)₂] group. The term“C₁-C₁₀-alkylsulfonyl” is a C₁-C₁₀-alkyl group, as defined above,attached via a sulfonyl [S(O)₂] group. C₁-C₂-Alkylsulfonyl ismethylsulfonyl or ethylsulfonyl. C₁-C₄-Alkylsulfonyl is additionally,for example, n-propylsulfonyl, 1-methylethylsulfonyl(isopropylsulfonyl), butylsulfonyl, 1-methylpropylsulfonyl(sec-butylsulfonyl), 2-methylpropylsulfonyl (isobutylsulfonyl) or1,1-dimethylethylsulfonyl (tert-butylsulfonyl). C₁-C₆-Alkylsulfonyl isadditionally, for example, pentylsulfonyl, 1-methylbutylsulfonyl,2-methylbutylsulfonyl, 3-methylbutylsulfonyl,1,1-dimethylpropylsulfonyl, 1,2-dinnethylpropylsulfonyl,2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl,1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl,4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl,1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl,2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl,3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl,1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl,1-ethyl-1-methylpropylsulfonyl or 1-ethyl-2-methylpropylsulfonyl.C₁-C₈-Alkylsulfonyl is additionally, for example, heptylsulfonyl,octylsulfonyl, 2-ethylhexylsulfonyl and positional isomers thereof.C₁-C₁₀-Alkylsulfonyl is additionally, for example, nonylsulfonyl,decylsulfonyl and positional isomers thereof.

The term “C₁-C₂-haloalkylsulfonyl” is a C₁-C₂-haloalkyl group, asdefined above, attached via a sulfonyl [S(O)₂] group. The term“C₁-C₄-haloalkylsulfonyl” is a C₁-C₄-haloalkyl group, as defined above,attached via a sulfonyl [S(O)₂] group. The term“C₁-C₈-haloalkylsulfonyl” is a C₁-C₈-haloalkyl group, as defined above,attached via a sulfonyl [S(O)₂] group. The term“C₁-C₁₀-haloalkylsulfonyl” is a C₁-C₁₀-haloalkyl group, as definedabove, attached via a sulfonyl [S(O)₂] group. C₁-C₂-Haloalkylsulfonylis, for example, S(O)₂CH₂F, S(O)₂CHF₂, S(O)₂CF₃, S(O)₂CH₂Cl, S(O)₂CHCl₂,S(O)₂CCl₃, chlorofluoromethylsulfonyl, dichlorofluoromethylsulfonyl,chlorodifluoromethylsulfonyl, 2-fluoroethylsulfonyl,2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl,2,2-difluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl,2-chloro-2-fluoroethylsulfonyl, 2-chloro-2,2-difluoroethylsulfonyl,2,2-dichloro-2-fluoroethylsulfonyl, 2,2,2-trichloroethylsulfonyl orS(O)₂C₂F₅. C₁-C₄-Haloalkylsulfonyl is additionally, for example,2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl,2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl,2-chloropropylsulfonyl, 3-chloropropylsulfonyl,2,3-dichloropropylsulfonyl, 2-bromopropylsulfonyl,3-bromopropylsulfonyl, 3,3,3-trifluoropropylsulfonyl,3,3,3-trichloropropylsulfonyl, S(O)₂CH₂—C₂F₅, S(O)₂CF₂—C₂F₅,1-(CH₂F)-2-fluoroethylsulfonyl, 1-(CH₂Cl)-2-chloroethylsulfonyl,1-(CH₂Br)-2-bromoethylsulfonyl, 4-fluorobutylsulfonyl,4-chlorobutylsulfonyl, 4-bromobutylsulfonyl or nonafluorobutylsulfonyl.C₁-C₆-Haloalkylsulfonyl is additionally, for example,5-fluoropentylsulfonyl, 5-chloropentylsulfonyl, 5-brompentylsulfonyl,5-iodopentylsulfonyl, undecafluoropentylsulfonyl, 6-fluorohexylsulfonyl,6-chlorohexylsulfonyl, 6-bromohexylsulfonyl, 6-iodohexylsulfonyl ordodecafluorohexylsulfonyl.

The term “3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturatedor aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms orheteroatom groups (if one or two or at most three heteroatoms of theheterocyclic ring are oxidzed) selected from N, O, S, NO, SO and SO₂, asring members” as used herein refers to monocyclic radicals, themonocyclic radicals being saturated, partially unsaturated or aromatic.The heterocyclic radical may be attached to the remainder of themolecule via a carbon ring member or via a nitrogen ring member.

Examples of 3-, 4-, 5-, 6- or 7-membered saturated heterocyclic ringinclude: Oxiranyl, aziridinyl, azetidinyl, 2-tetrahydrofuranyl,3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl,2-pyrrolidinyl, 3-pyrrolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl,5-pyrazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 2-oxazolidinyl,4-oxazolidinyl, 5-oxazolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl,5-isoxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl,3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl,1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl,1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl,1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl,1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2-tetrahydropyranyl,4-tetrahydropyranyl, 1,3-dioxan-5-yl, 1,4-dioxan-2-yl, 2-piperidinyl,3-piperidinyl, 4-piperidinyl, 3-hexahydropyridazinyl,4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl,5-hexahydropyrimidinyl, 2-piperazinyl, 1,3,5-hexahydrotriazin-2-yl and1,2,4-hexahydrotriazin-3-yl, 2-morphollnyl, 3-morpholinyl,2-thiomorpholinyl, 3-thiomorpholinyl, 1-oxothiomorpholin-2-yl,1-oxothiomorpholin-3-yl, 1,1-dioxothiomorpholin-2-yl,1,1-dioxothiomorpholin-3-yl, hexahydroazepin-1-, -2-, -3- or -4-yl,hexahydrooxepinyl, hexahydro-1,3-diazepinyl, hexahydro-1,4-diazepinyl,hexahydro-1,3-oxazepinyl, hexahydro-1,4-oxazepinyl,hexahydro-1,3-dioxepinyl, hexahydro-1,4-dioxepinyl and the like.

Examples of 3-, 4-, 5-, 6- or 7-membered partially unsaturatedheterocyclic ring include: 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl,2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl,2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl,2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl,2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl,2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl,2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl,2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl,2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl,2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl,2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl,2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl,2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl,3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl,3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl,4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl,4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl,2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl,3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl,3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl,2-, 3-, 4-, 5- or 6-di- or tetrahydropyridinyl, 3-di- ortetrahydropyridazinyl, 4-di- or tetrahydropyridazinyl, 2-di- ortetrahydropyrimidinyl, 4-di- or tetrahydropyrimidinyl, 5-di- ortetrahydropyrimidinyl, di- or tetrahydropyrazinyl, 1,3,5-di- ortetrahydrotriazin-2-yl, 1,2,4-di- or tetrahydrotriazin-3-yl,2,3,4,5-tetrahydro[1H]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl,3,4,5,6-tetrahydro[2H]azepin-2-, -3-, -4-, -5-, -6- or -7-yl,2,3,4,7-tetrahydro[1′-1]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl,2,3,6,7-tetrahydro[1H]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl,tetrahydrooxepinyl, such as 2,3,4,5-tetrahydro[1H]oxepin-2-, -3-, -4-,-5-, -6- or 2,3,4,7-tetrahydro[1H]oxepin-2-, -3-, -4-, -5-, -6- or-7-yl, 2,3,6,7-tetrahydro[1H]oxepin-2-, -3-, -4-, -5-, -6- or -7-yl,tetrahydro-1,3-diazepinyl, tetrahydro-1,4-diazepinyl,tetrahydro-1,3-oxazepinyl, tetrahydro-1,4-oxazepinyl,tetrahydro-1,3-dioxepinyl and tetrahydro-1,4-dioxepinyl.

3-, 4-, 5-, 6- or 7-membered aromatic heterocyclic ring is 5- or6-membered aromatic heterocyclic (hetaryl). Examples are: 2-furyl,3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl,4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl,2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl,1,3,4-triazol-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl,3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl,5-pyrimidinyl and 2-pyrazinyl.

The remarks made below concerning preferred embodiments of the variablesof the compounds of formula I, especially with respect to theirsubstituents A¹, A², A³, A⁴, R¹, R², R³, R⁴, R^(5a), R^(5b), R^(5c),R^(5d), R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹², R^(c), R^(n), R^(o), m, and p thefeatures of the use and method according to the invention and of thecomposition of the invention are valid both on their own and, inparticular, in every possible combination with each other.

The radical A when used in the text is as following defined:

wherein # denotes the binding site to the remainder of formula I andwherein the variables p, R³, R⁴, A¹, A², A³ and A⁴ are as defined informula I.

As a matter of course, the p radicals R⁴ replace a hydrogen atom on acarbon ring atom. For instance, if A¹, A², A³ or A⁴ is defined to be CHand if this position is to be substituted by a radical R⁴, then A¹, A²,A³ or A⁴ is of course a substituted C—R⁴. If there is more than oneradical R⁴, these substituents R⁴ can be the same or different.

Preferably, at most two of A¹, A², A³ and A⁴ are N.

In a preferred embodiment, A′, A², A³ and A⁴ are CR⁴. In the case thatmore than one substituent R⁴ is present in the radical A, the differentR⁴ are selected independently from each other. In case p is 2, the twosubstituents R⁴ are preferably bound on the position of A¹ and A². Incase p is 1, the substituent R⁴ is preferably bound on the position ofA¹ or A².

In analogy to the above cited meaning of A, A³ and A⁴ are respectivelyequivalent to A² and A¹ and thus have the same definition ofpreferencies.

Preferably, three of A¹, A², A³ and A⁴ are CH and the remaining radicalis a substituted CR⁴. Even more preferably, A², A³, A⁴ and A¹ are CH.

In one embodiment,

-   R³ is selected from the group consisting of hydrogen, halogen,    cyano, azido, nitro, SCN, SF₅, C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl,    C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl,    -   wherein the carbon atoms of the aforementioned aliphatic and        cycloaliphatic radicals may be unsubstituted or substituted with        one or more R⁶;    -   Si(R¹¹)₂R¹², OR⁷, S(O)_(m)R⁷, N(R⁸)R⁹, N═C(R⁶)₂, C(═O)R⁶,        C(═S)R⁶, C(═NR⁸)R⁶, phenyl which may be substituted by 1, 2, 3,        4 or 5 radicals R¹⁰; and    -   a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,        -   wherein said heterocyclic ring            -   is saturated, partially unsaturated or aromatic,            -   comprises 1, 2 or 3 heteroatoms or heteroatom groups                selected from N, O, S, NO, SO and SO₂,            -   is unsubstituted or substituted by one to five radicals                R¹⁰ and wherein one or two CH₂ groups in said saturated                or partially saturated heterocyclic rings may be                replaced by one or two C═O groups.

In another embodiment, R³ is selected from the group consisting ofhydrogen, halogen, cyano, azido, nitro, SCN, SF₅, C₁-C₆-alkyl,C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-cycloalkoxy wherein the last fourmentioned radicals are preferably at least substituted by one halogen,Si(R¹¹)₂R¹², OR⁷, S(O)_(m)R⁷, N(R⁸)R⁹, N═C(R⁶)₂, C(═O)R⁶, C(═S)R⁶ andC(═NR⁸)R⁶.

Within these embodiments, R³ is preferably selected from the groupconsisting of hydrogen, halogen, cyano, nitro, SR⁷, C₁-C₆-alkyl,C₃-C₆-cycloalkyl, C₁-C₆-alkoxy and C₃-C₆-cycloalkoxy wherein the fourlast mentioned group are preferably at least substituted by one halogenand wherein the five last mentioned radicals may be substituted by oneto five radicals R⁶.

More preferably, R³ is selected from the group consisting of halogen,cyano, nitro, C₁-C₆-alkyl, C₁-C₆-alkoxy wherein the two last mentionedradicals are at least substituted by one halogen.

Even more preferably, R³ is selected from the group consisting offluorine, chlorine, bromine, iodine, cyano, NO₂, CF₃, CHF₂, CH₂F, CF₂Cl,CFCl₂, CCl₃, OCF₃, OCHF₂ and OCF₂CHF₂.

More particularly, R³ is preferably fluorine or chlorine or bromine.

In an embodiment,

-   R⁴ is selected independently from the group consisting of hydrogen,    halogen, cyano, azido, nitro, SCN, SF₅, C₁-C₁₀ alkyl,    C₃-C₈-cycloalkyl, C₂-C₁₀-alkenyl, alkynyl, wherein the carbon atoms    of the aforementioned aliphatic and cycloaliphatic radicals may be    unsubstituted or substituted with one or more R⁶;    -   Si(R¹¹)₂R¹², OR⁷, S(O)_(m)R⁷, N(R⁸)R⁹, N═C(R⁶)₂, C(═O)R⁶,        C(═S)R⁶, C(═NR⁸)R⁶, C(═O)N(R⁸)R⁹, C(═S)N(R⁸)R⁹, phenyl which may        be substituted by 1, 2, 3, 4 or 5 radicals R¹⁰; and    -   a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,    -   wherein said heterocyclic ring        -   is saturated or partially unsaturated or aromatic,        -   comprises 1, 2 or 3 heteroatoms or heteroatom groups            selected from N, O, S, NO, SO and SO₂        -   is unsubstituted or substituted by one to five radicals R¹⁰            and        -   wherein one or two CH₂ groups in said saturated or partially            saturated heterocyclic rings may be replaced by one or two            C═O groups;    -   or two radicals R⁴ bound on adjacent carbon atoms together form        a group selected from —CH₂CH₂CH₂CH₂—, —CH═CH—CH═CH—,        —N═CH—CH═CH—, —CH═N—CH═CH—, —N═CH—N═CH—, —OCH₂CH₂CH₂—,        —OCH═CHCH₂—, —CH₂OCH₂CH₂—, —OCH₂CH₂O—, —OCH₂OCH₂—, —CH₂CH₂CH₂—,        —CH—CHCH₂—, —CH₂CH₂O, —CH═CHO—, —CH₂OCH₂—, —CH₂C(═O)O—,        —C(═O)OCH₂—, —O(CH₂)O, —SCH₂CH₂CH₂—, —SCH═CHCH₂—, —CH₂SCH₂CH₂—,        —SCH₂CH₂S—, —SCH₂SCH₂—, —CH₂CH₂S—, —CH═CHS—, —CH₂SCH₂—,        —CH₂C(═S)S—, —C(═S)SCH₂—, —S(CH₂)S—, —CH₂CH₂NR⁸—, —CH₂CH═N—,        —CH═CH—NR⁸—, —OCH═N— and —SCH═N—, wherein in each of the above        groups one to five hydrogen atoms may be replaced by one to five        substituents selected from halogen, methyl, halomethyl,        hydroxyl, methoxy and halomethoxy or one or two CH₂ groups of        the above groups may be replaced by one or two C═O groups.

In another embodiment,

-   R⁴ is selected from the group consisting of hydrogen, halogen,    cyano, azido, nitro, SCN, SF₅, C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl,    C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl,    -   wherein the carbon atoms of the aforementioned aliphatic and        cycloaliphatic radicals may be unsubstituted or substituted with        one or more R⁶;    -   Si(R¹¹)₂R¹², OR⁷, S(O)_(m)R⁷, N(R⁸)R⁹, N═C(R⁶)₂, C(═O)R⁶,        C(═S)R⁶, C(═NR⁸)R⁶, C(═O)N(R⁸)R⁹, C(═S)N(R⁸)R⁹, phenyl,        -   which may be substituted by 1, 2, 3, 4 or 5 radicals R¹⁰;            and    -   a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,        -   wherein said heterocyclic ring            -   is saturated or partially unsaturated or aromatic,            -   comprises 1, 2 or 3 heteroatoms or heteroatom groups                selected from N, O, S, NO SO and SO₂,            -   is unsubstituted or substituted by one to five radicals                R¹⁰ and            -   wherein one or two CH₂ groups in said saturated or                partially saturated rings may be replaced by one or two                C═O groups.

In a further embodiment,

-   R⁴ is selected from the group consisting of hydrogen, halogen,    cyano, azido, nitro, SCN, SF₅, C₃-C₅-cycloalkyl, C₂-C₁₀-alkenyl,    C₂-C₁₀-alkynyl,    -   wherein the carbon atoms of the aforementioned aliphatic and        cycloaliphatic radicals may be unsubstituted or substituted with        one or more R⁶;    -   Si(R¹¹)₂R¹², OR⁷, S(O)_(m)R⁷, N(R⁸)R⁹, N═C(R⁶)₂, C(═O)R⁶,        C(═S)R⁶, C(═NR⁸)R⁶, C(═O)N(R⁸)R⁹ and C(═S)N(R⁸)R⁹.

Within these embodiments, R⁴ is preferably selected from the groupconsisting of hydrogen, halogen, cyano, nitro, C₁-C₆-alkyl,C₃-C₆-cycloalkyl, C₁-C₆-alkoxy and C₁-C₆-cycloalkoxy wherein the fourlast mentioned radicals if substituted are preferably substituted by onehalogen and wherein the five last mentioned groups may be substituted byone to five radicals R⁶.

More preferably, R⁴ is selected from the group consisting of hydrogen,halogen, cyano, nitro, C₁-C₆-alkyl and C₁-C₆-haloalkyl.

Even more preferably, R⁴ is selected from the group consisting ofhydrogen, fluorine, chlorine, bromine, iodine, CF₃ and CHF₂.

More particularly, R⁴ is hydrogen.

Examples of suitable radicals A are the radicals numbered A1a1 to A1a98which are radicals of the formula A as above depicted wherein A², A³, A⁴are CH, A¹ is CR⁴, and R⁴ and R³ are as defined in one row of thefollowing Table B (radicals A1a1 to A1a98):

TABLE B Radical A R³ R⁴ A1a1 F H A1a2 Cl H A1a3 Br H A1a4 I H A1a5 CN HA1a6 NO₂ H A1a7 CF₃ H A1a8 CHF₂ H A1a9 CH₂F H A1a10 CF₂Cl H A1a11 CFCl₂H A1a12 CCl₃ H A1a13 OCHF₂ H A1a14 SCF₃ H A1a15 F F A1a16 Cl F A1a17 BrF A1a18 I F A1a19 CN F A1a20 NO₂ F A1a21 CF₃ F A1a22 CHF₂ F A1a23 CH₂F FA1a24 CF₂Cl F A1a25 CFCl₂ F A1a26 CCl₃ F A1a27 OCHF₂ F A1a28 SCF₃ FA1a29 F Cl A1a30 Cl Cl A1a31 Br Cl A1a32 I Cl A1a33 CN Cl A1a34 NO₂ ClA1a35 CF₃ Cl A1a36 CHF₂ Cl A1a37 CH₂F Cl A1a38 CF₂Cl Cl A1a39 CFCl₂ ClA1a40 CCl₃ Cl A1a41 OCHF₂ Cl A1a42 SCF₃ Cl A1a43 F Br A1a44 Cl Br A1a45Br Br A1a46 I Br A1a47 CN Br A1a48 NO₂ Br A1a49 CF₃ Br A1a50 CHF₂ BrA1a51 CH₂F Br A1a52 CF₂Cl Br A1a53 CFCl₂ Br A1a54 CCl₃ Br A1a55 OCHF₂ BrA1a56 SCF₃ Br A1a57 F CN A1a58 Cl CN A1a59 Br CN A1a60 I CN A1a61 CN CNA1a62 NO₂ CN A1a63 CF₃ CN A1a64 CHF₂ CN A1a65 CH₂F CN A1a66 CF₂Cl CNA1a67 CFCl₂ CN A1a68 CCl₃ CN A1a69 OCHF₂ CN A1a70 SCF₃ CN A1a71 F MeA1a72 Cl Me A1a73 Br Me A1a74 I Me A1a75 CN Me A1a76 NO₂ Me A1a77 CF₃ MeA1a78 CHF₂ Me A1a79 CH₂F Me A1a80 CF₂Cl Me A1a81 CFCl₂ Me A1a82 CCl₃ MeA1a83 OCHF₂ Me A1a84 SCF₃ Me A1a85 F CF₃ A1a86 Cl CF₃ A1a87 Br CF₃ A1a88I CF₃ A1a89 CN CF₃ A1a90 NO₂ CF₃ A1a91 CF₃ CF₃ A1a92 CHF₂ CF₃ A1a93 CH₂FCF₃ A1a94 CF₂Cl CF₃ A1a95 CFCl₂ CF₃ A1a96 CCl₃ CF₃ A1a97 OCHF₂ CF₃ A1a98SCF₃ CF₃

Analog to the above listed Table B, further examples of suitableradicals A are the radicals of the formula A numbered A1a99 to A1a197wherein A¹, A³, A⁴ are CH, A² is CR⁴, and R⁴ and R³ for each radical Ahave the meaning of one line in Table B.

In a particular embodiment of the invention, each example of radical Anumbered A1a1 to A1a197 is a preferred radical A in formula I.

In an embodiment,

-   R^(5a) is selected from the group consisting of hydrogen, halogen,    cyano, azido, nitro, —SCN, SF₅, C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl,    C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl,    -   wherein the carbon atoms of the aforementioned aliphatic and        cycloaliphatic radicals may be unsubstituted or substituted with        one or more R⁶,    -   Si(R¹¹)₂R¹², OR⁷, S(O)_(m)R⁷, N(R⁸)R⁹, N═C(R⁶)₂, C(═O)R⁶,        C(═S)R⁶, C(═NR⁸)R⁶, phenyl,        -   which may be substituted by 1, 2, 3, 4 or 5 radicals R¹⁰;    -   and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring        -   wherein said heterocyclic ring            -   is saturated or partially unsaturated or aromatic,            -   comprises 1, 2 or 3 heteroatoms or heteroatom groups                selected from N, O, S, NO, SO and SO₂,            -   is unsubstituted or substituted by one to five radicals                R¹⁰, and            -   wherein one or two CH₂ groups in said saturated or                partially saturated rings may be by one or two C═O                groups;-   or R^(5a) may form together with the adjacent carbon atom R^(5b) a    5- or 6-membered ring which is at least substituted by one halogen.

More preferably,

-   R^(5a) is selected from the group consisting of hydrogen, halogen,    cyano, azido, nitro, C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl, C₂-C₁₀-alkenyl,    C₂-C₁₀-alkynyl,    -   wherein the carbon atoms of the aforementioned aliphatic and        cycloaliphatic radicals may be unsubstituted or substituted with        one or more R⁶;    -   Si(R¹¹)₂R¹², OR⁷, S(O)_(m)R⁷, N(R⁸)R⁹, N═C(R⁶)₂, C(═O)R⁶,        C(═S)R⁶ and C(═NR⁸)R⁶.

More preferably, R^(5a) is selected from the group consisting ofhydrogen, halogen, cyano, nitro, SCF₃, SOCF₃, C₁-C₆-alkyl,C₃-C₆-cycloalkyl, C₁-C₆-alkoxy and C₁-C₆-cycloalkoxy wherein the lastfour mentioned radicals may be substituted by one halogen.

More preferably, R^(5a) is selected from the group consisting ofhydrogen, halogen, cyano, nitro, C₁-C₆-alkyl, C₃-C₆-cycloalkyl,C₁-C₆-alkoxy (e.g. OCF₃, OCHF₂, OCF₂CHF₂) and C₁-C₆-cycloalkoxy whereinthe five last mentioned group may be substituted by halogen.

Even more preferably, R^(5a) is selected from the group consisting ofhydrogen, halogen, C₁-C₆-alkyl and C₁-C₆-haloalkyl.

Even more preferably, R^(5a) is selected from the group consisting ofhydrogen, fluorine, chlorine, bromine, iodine, CH₃, CF₃, CHF₂, CH₂F,CF₂Cl, CFCl₂ and CCl₃.

Even more preferably, R^(5a) is selected from the group consisting ofhydrogen, fluorine, chlorine, bromine, iodine, CF₃ and CHF₂.

More particularly, R^(5a) is hydrogen.

In a embodiment,

-   R^(5b) is selected from the group consisting of C₁-C₆-alkyl,    C₃-C₆-cycloalkyl, alkoxy and C₁-C₆-cycloalkoxy, wherein each    mentioned radical    -   is at least substituted with one halogen,    -   may be further partially or fully halogenated and    -   may be substituted with one to five radicals R⁶;-   or may form together with the adjacent carbon atom R^(5c) or R^(5a)    a 5- or 6-membered ring which is at least substituted with one    halogen.

Within the above embodiment, R^(5b) is preferably selected from thegroup consisting of C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy andC₁-C₆-cycloalkoxy and wherein each mentioned radical is at leastsubstituted with one halogen.

Within the above embodiments, R^(5b) is preferably selected from thegroup consisting of C₁-C₆-haloalkyl and C₁-C₆-haloalkoxy.

Even more preferably, R^(5b) is selected from the group consisting ofCF₃, CHF₂, CH₂F, CF₂F₃, CF(CF₃)₂, COH(CF₃)₂, CF₂Cl, CFCl₂, CCl₃, OCF₃,OCHF₂, OCF₂CF₃, OCF₂CHF₂, OCF(CF₃)₂, OCF₂Cl, OCFCl₂ and OCCl₃.

Even more preferably, R^(5b) is selected from the group consisting ofCF₃, CHF₂, CF₂F₃, CF(CF₃)₂, COH(CF₃)₂, CF₂Cl, CFCl₂, CCl₃, OCF₃, OCHF₂,OCF₂CF₃, OCF₂CHF₂, OCF(CF₃)₂, OCF₂Cl, OCFCl₂ and OCCl₃.

More particularly R^(5b) is CF₃.

Preferably, R^(5c) is selected from the group consisting of hydrogen,halogen, C₁-C₆-alkyl, C₃-C₈-cycloalkyl, C₂-C₆-alkenyl and C₂-C₆-alkynyl,wherein the last four mentioned groups may be partially or fullyhalogenated and/or may be substituted with one to five radicals R⁶.

More preferably, R^(5c) is selected from the group consisting ofhydrogen, halogen, C₁-C₆-alkyl and C₁-C₆-haloalkyl.

More particularly, R^(5c) is hydrogen.

Preferably, R^(5d) is selected from the group consisting of hydrogen,halogen, C₁-C₆-alkyl, C₃-C₈-cycloalkyl, C₂-C₆-alkenyl and C₂-C₆-alkynyl,wherein the last four mentioned groups may be partially or fullyhalogenated and/or may be substituted with one to five radicals R⁶.

More preferably, R^(5d) is selected from the group consisting ofhydrogen, halogen, C₁-C₆-alkyl and C₁-C₆-haloalkyl.

More particularly, R^(5d) is hydrogen.

In case R⁶ is a substituent on an alkyl, alkenyl or alkynyl group, it ispreferably selected from the group consisting of

-   -   hydrogen, halogen, cyano, azido, nitro, SCN, SF₅, C₁-C₆-alkyl,        C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl,        C₁-C₆-alkylsulfonyl, C₃-C₈-cycloalkyl,        C₃-C₈-cycloalkyl-C₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,    -   wherein the carbon atom of the aforementioned aliphatic and        cycloaliphatic radicals may be substituted with one or more        R^(c);    -   Si(R¹¹)₂R¹², OR^(o), O(CO)R^(c), O(CS)R^(c), S(O)_(m)R^(c),        S(O)_(m)N(R^(n))₂, S(CO)R^(c), S(CS)R^(c), S(C═NR^(n))R^(c),        N(R^(n))₂, N(R^(n))C(═O)R^(c), N(R^(n))C(═S)R^(c),        NS(O)_(n)R^(c), N═C(R^(c))₂, C(═O)R^(c), C(═S)R^(c),        C(═NR^(n))R^(c), C(═O)N(R^(n))₂, C(═S)N(R^(n))₂, phenyl,        -   which may be substituted by 1, 2, 3, 4 or 5 radicals R¹⁰,            and    -   a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,        -   wherein said heterocyclic ring            -   is saturated or partially unsaturated or aromatic,            -   comprises 1, 2 or 3 heteroatoms or heteroatom groups                selected from N, O, S, NO, SO and SO₂,            -   is unsubstituted or substituted with one to five                radicals R¹⁰, and            -   wherein one or two CH₂ groups in said saturated or                partially saturated heterocyclic rings may be replaced                by one or two C═O groups.

In case R⁶ is a substituent on an alkyl, alkenyl or alkynyl group, it ismore preferably selected from the group consisting of

-   -   halogen, cyano, C₃-C₈-cycloalkyl, C₃-C₅-halocycloalkyl, OR^(o),        SR^(o), phenyl, which may be substituted with 1, 2, 3, 4 or 5        radicals R¹⁰, and    -   a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,        -   wherein said heterocyclic ring            -   is saturated or partially unsaturated or aromatic,            -   comprises 1, 2 or 3 heteroatoms or heteroatom groups                selected from N, O, S, NO, SO and SO₂,        -   is unsubstituted or substituted with one or more radicals            R¹⁰;    -   wherein R^(o) and R¹⁰ have one of the meanings given above or in        particular one of the preferred meanings given below.

In case R⁶ is a substituent on an alkyl, alkenyl or alkynyl group, it iseven more preferably selected from the group consisting of halogen,cyano, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, phenyl which maybe substituted with 1, 2, 3, 4 or 5 radicals R¹⁰, and a 5- or 6-memberedheteroaromatic ring containing 1, 2 or 3 heteroatoms selected from N, Oand S, wherein the heteroaromatic ring may be substituted with one ormore radicals R¹⁰; and

wherein R¹⁰ has one of the meanings given above or in particular one ofthe preferred meanings given below.

In case R⁶ is a substituent on an alkyl, alkenyl or alkynyl group, it isin particular selected from the group consisting of halogen and a 5- or6-membered heteroaromatic ring containing 1, 2 or 3 heteroatoms selectedfrom N, O and S, wherein the heteroaromatic ring is unsubstituted orsubstituted with one or more radicals R¹⁰; and

wherein R¹⁰ has one of the meanings given above or in particular one ofthe preferred meanings given below.

In case R⁶ is a substituent on a cycloalkyl group, it is preferablyselected from the group consisting of halogen, cyano, azido, nitro, SCN,SF₅, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl,C₃-C₈-cycloalkyl, C₃-C₆-halocycloalkyl, C₂-C₆-alkenyl,C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, Si(R¹¹)₂R¹²,OR^(o), O(CO)R^(c), O(CS)R^(c), S(O)_(m)R^(c), S(O)_(m)N(R^(n))₂,S(CO)R^(c), S(CS)R^(c), S(C═NR^(n))R^(c), N(R^(n))₂, N(R^(n))C(═O)R^(c),N(R^(n))C(═S)R^(c), NS(O)_(m)R^(c), N═C(R⁸)₂, C(═O)R^(c), C(═S)R^(c),C(═NR^(n))R^(c), C(═O)N(R^(n))₂, C(═S)N(R^(n))₂, phenyl which may besubstituted by 1, 2, 3, 4 or 5 radicals R¹⁰, and a 3-, 4-, 5-, 6- or7-membered heterocyclic ring, wherein said heterocyclic ring issaturated or partially unsaturated or aromatic, comprises 1, 2 or 3heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO₂and wherein said heterocyclic ring is unsubstituted or substituted withone or more radicals R¹⁰;

or two vicinally bound radicals R⁶ together form a group selected from═C(R^(c))₂, S(O)_(m)R^(c), ═S(O)_(m)N(R^(n))₂, ═NR^(n), and ═NN(R^(n))₂;or two radicals R⁶, together with the carbon atoms to which they arebound, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partiallyunsaturated carbocyclic or heterocyclic ring containing 1, 2 or 3heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO₂;wherein R^(c), R^(n), R^(o), R¹⁰, R¹¹ and R¹² have one of the meaningsgiven above or in particular one of the preferred meanings given below.

In case R⁶ is a substituent on a cycloalkyl group, it is more preferablyselected from the group consisting of halogen, cyano, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, OR^(o), SR^(o),S(O)_(m)R^(o), S(O)_(m)N(R^(n))₂, N(R^(n))₂, C(═O)N(R^(n))₂,C(═S)N(R^(n))₂, C(═O)R^(o), phenyl which may be substituted by 1, 2, 3,4 or 5 radicals R¹⁰, and a 3-, 4-, 5-, 6- or 7-membered saturated,partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO₂,as ring members, where the heterocyclic ring may be substituted with oneor more radicals R¹⁰;

wherein R^(c), R^(n), R^(o) and R¹⁰ have one of the meanings given aboveor in particular one of the preferred meanings given below.

In case R⁶ is a substituent on a cycloalkyl group, it is even morepreferably selected from the group consisting of halogen, C₁-C₄-alkyl,C₁-C₃-haloalkyl, C₁-C₄-alkoxy and C₁-C₃-haloalkoxy. In particular, R⁶ asa substituent on a cycloalkyl group is selected from halogen,C₁-C₄-alkyl and C₁-C₃-haloalkyl.

In case R⁶ is a substituent on C(═O), C(═S) or C(═NR⁸), it is preferablyselected from the group consisting of hydrogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₆-alkoxy C₁-C₆-alkyl, C₃-C₈-cycloalkyl,C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,C₂-C₆-haloalkynyl, —OR^(o), —SR^(o), —N(R^(n))₂, phenyl which may besubstituted by 1, 2, 3, 4 or 5 radicals R¹⁰, and a 3-, 4-, 5-, 6- or7-membered saturated, partially unsaturated or aromatic heterocyclicring containing 1, 2 or 3 heteroatoms or heteroatom groups selected fromN, O, S, NO, SO and SO₂, wherein the heterocyclic ring may besubstituted with one or more radicals R¹⁰;

wherein R^(c), R^(n), R^(o) and R¹⁰ have one of the meanings given aboveor in particular one of the preferred meanings given below.

In case R⁶ is a substituent on C(═O), C(═S) or C(═NR⁸), it is morepreferably selected from the group consisting of C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy, phenyl which may be substituted by 1, 2, 3, 4 or 5radicals R¹⁰, and a 3-, 4-, 5-, 6- or 7-membered saturated, partiallyunsaturated or aromatic heterocyclic ring containing 1, 2 or 3heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO₂,wherein the heterocyclic ring may be substituted by one or more radicalsR¹⁰;

wherein R¹⁰ has one of the meanings given above or in particular one ofthe preferred meanings given below.

In case R⁶ is a substituent on C(═O), C(═S) or C(═NR⁸), it is even morepreferably selected from the group consisting of C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₁-C₄-alkoxy,C₁-C₃-haloalkoxy, phenyl which may be substituted with 1, 2, 3, 4 or 5radicals R¹⁰, and a 5- or 6-membered heteroaromatic ring containing 1, 2or 3 heteroatoms selected from N, O and S, wherein the heteroaromaticring may be substituted with one or more radicals R¹⁰;

wherein R¹⁰ has one of the meanings given above or in particular one ofthe preferred meanings given below.

Preferably, each R⁷ is independently selected from the group consistingof hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl,C₃-C₈-halocycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl, phenyl which may besubstituted by 1, 2, 3, 4 or 5 radicals R¹⁰; and a 3-, 4-, 5-, 6- or7-membered saturated, partially unsaturated or aromatic heterocyclicring containing 1, 2 or 3 heteroatoms or heteroatom groups selected fromN, O, S, NO, SO and SO₂, wherein the heterocyclic ring is unsubstitutedor substituted with. 1, 2, 3 or 4, preferably 1 or 2, more preferably 1,radicals R¹⁰, wherein R¹⁰ has one of the meanings given above or inparticular one of the preferred meanings given below.

More preferably, each R⁷ is independently selected from the groupconsisting of hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, phenyl which isunsubstituted or substituted by 1, 2, 3, 4 or 5 radicals R¹⁰; and a 5-or 6-membered heteroaromatic ring containing 1, 2 or 3 heteroatomsselected from N, O and S, wherein the heteroaromatic ring may besubstituted by one or more radicals R¹⁰; where R¹⁰ has one of themeanings given above or in particular one of the preferred meaningsgiven below.

R⁸ and R⁹ are independently of each other and independently of eachoccurrence preferably selected from the group consisting of hydrogen,C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl,phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R¹⁰, and a3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated oraromatic heterocyclic ring containing 1, 2 or 3 heteroatoms orheteroatom groups selected from N, O, S, NO, SO and SO₂, where theheterocyclic ring may be substituted by one or more radicals R¹⁰; andwherein R¹⁰ has one of the meanings given above or in particular one ofthe preferred meanings given below.

R⁸ and R⁹ are independently of each other and independently of eachoccurrence more preferably selected from the group consisting ofhydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, phenyl which may be substitutedby 1, 2, 3, 4 or 5 radicals R¹⁰, and a 5- or 6-membered heteroaromaticring containing 1, 2 or 3 heteroatoms selected from N, O and S, as ringmembers, wherein the heteroaromatic ring is unsubstituted or substitutedby one or more radicals R¹⁰; and wherein R¹⁰ has one of the meaningsgiven above or in particular one of the preferred meanings given below.

In particular, R⁸ and R⁹ are independently of each other andindependently of each occurrence selected from the group consisting ofhydrogen and C₁-C₄-alkyl. Preferably, each R¹⁰ is independently selectedfrom the group consisting of halogen, cyano, C₁-C₁₀-alkyl which may bepartially or fully halogenated and/or may be substituted by one or moreradicals R^(c), C₃-C₈-cycloalkyl which may be partially or fullyhalogenated and/or may be substituted by one or more radicals R^(c),OR^(o), O(CO)R^(c), O(CS)R^(c), S(O)_(m)R^(o), S(O)_(m)N(R^(n))₂,N(R^(n))₂, C(═O)R^(c), C(═O)N(R^(n))₂, phenyl which may be substitutedby 1, 2, 3, 4 or 5 radicals independently selected from halogen, cyano,nitro, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy;and a 3-, 4-, 5-, 6- or 7-membered saturated or unsaturated heterocyclicring containing 1, 2 or 3 heteroatoms or heteroatom groups selected fromN, O, S, NO, SO and SO₂, as ring members, which may be substituted byone or more radicals independently selected from halogen, cyano, nitro,C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy;

or two radicals R¹⁰ bound on adjacent atoms together form a groupselected from —CH₂CH₂CH₂CH₂—, —CH═CH—CH═CH—, —N═CH—CH═CH—, —CH═N—CH═CH—,—N═CH—N═CH—, —OCH₂CH₂CH₂—, —OCH═CHCH₂—, —CH₂OCH₂CH₂—, —OCH₂CH₂O—,—OCH₂OCH₂—, —CH₂CH₂CH₂—, —CH═CHCH₂—, —CH₂CH₂O—, —CH═CHO—, —CH₂OCH₂—,—CH₂C(═O)O—, —C(═O)OCH₂—, and —O(CH₂)O—, thus forming, together with theatoms to which they are bound, a 5- or 6-membered ring, where thehydrogen atoms of the above groups may be replaced by one or moresubstituents selected from halogen, methyl, halomethyl, hydroxyl,methoxy and halomethoxy or one or more CH₂ groups of the above groupsmay be replaced by a C═O group,where R^(c), R^(n) and R^(o) have one of the general or in particularone of the preferred meanings given above.

More preferably, each R¹⁰ is independently selected from the groupconsisting of halogen, cyano, C₁-C₁₀-alkyl which may be partially orfully halogenated and/or may be substituted by one or more radicalsR^(c), —OR^(n), —N(R^(n))₂, C(═O)R^(c), —C(═O)OR^(c), —C(═O)N(R^(n))₂,phenyl which may be substituted by 1, 2, 3, 4 or 5 radicalsindependently selected from halogen, cyano, nitro, C₁-C₆-alkyl,C₁-C₆-alkoxy and C₁-C₆-haloalkoxy; and a 3-, 4-, 5-, 6- or 7-memberedsaturated or unsaturated heterocyclic ring containing 1, 2 or 3heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO₂,as ring members, which may be substituted by one or more radicalsindependently selected from halogen, cyano, nitro, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy;

where R^(c), R^(n), R^(o) have one of the general or in particular oneof the preferred meanings given above.

Even more preferably, each R¹⁰ is independently selected from the groupconsisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy andC₁-C₄-haloalkoxy. In particular, each R¹⁰ is independently selected fromthe group consisting of halogen, C₁-C₄-alkyl and C₁-C₄-haloalkyl and isspecifically halogen, more specifically chlorine.

Preferably, R¹¹ and R¹² are, independently of each other andindependently of each occurrence, selected from C₁-C₄-alkyl and are inparticular methyl.

A very preferred embodiment of the invention relates to the compounds ofthe formula (I-a)

whereinA has one of the general meaning as defined here above;A is in particular one of the preferred radical A numbered A1a1 toA1a197 as defined in table B above.R^(5b), R^(5a), R¹ and R² have one of the general meaning or one of thepreferred meaning as here above defined.

In particular, R^(5b), R¹, and R² have the meaning Ib numbered Ib1 toIb1168 as defined in each line of the following Table C. It is to notethat R¹ and R² are permutable in the meaning of Ib1009 to Ib1168.

TABLE C Ib R^(5b) R¹ R² Ib1 CF₃ Me Me Ib2 CHF₂ Me Me Ib3 CF₂CF₃ Me MeIb4 CF(CF₃)₂ Me Me Ib5 COH(CF₃)₂ Me Me Ib6 CF₂Cl Me Me Ib7 CFCl₂ Me MeIb8 CCl₃ Me Me Ib9 OCF₃ Me Me Ib10 OCHF₂ Me Me Ib11 OCF₂CF₃ Me Me Ib12OCF₂CHF₂ Me Me Ib13 OCF(CF₃)₂ Me Me Ib14 OCF₂Cl Me Me Ib15 OCFCl₂ Me MeIb16 OCCl₃ Me Me Ib17 CF₃ Me Et Ib18 CHF₂ Me Et Ib19 CF₂CF₃ Me Et Ib20CF(CF₃)₂ Me Et Ib21 COH(CF₃)₂ Me Et Ib22 CF₂Cl Me Et Ib23 CFCl₂ Me EtIb24 CCl₃ Me Et Ib25 OCF₃ Me Et Ib26 OCHF₂ Me Et Ib27 OCF₂CF₃ Me Et Ib28OCF₂CHF₂ Me Et Ib29 OCF(CF₃)₂ Me Et Ib30 OCF₂Cl Me Et Ib31 OCFCl₂ Me EtIb32 OCCl₃ Me Et Ib33 CF₃ Me Pr Ib34 CHF₂ Me Pr Ib35 CF₂CF₃ Me Pr Ib36CF(CF₃)₂ Me Pr Ib37 COH(CF₃)₂ Me Pr Ib38 CF₂Cl Me Pr Ib39 CFCl₂ Me PrIb40 CCl₃ Me Pr Ib41 OCF₃ Me Pr Ib42 OCHF₂ Me Pr Ib43 OCF₂CF₃ Me Pr Ib44OCF₂CHF₂ Me Pr Ib45 OCF(CF3)2 Me Pr Ib46 OCF₂Cl Me Pr Ib47 OCFCl₂ Me PrIb48 OCCl₃ Me Pr Ib49 CF₃ Me iPr Ib50 CHF₂ Me iPr Ib51 CF₂CF₃ Me iPrIb52 CF(CF₃)₂ Me iPr Ib53 COH(CF₃)₂ Me iPr Ib54 CF₂Cl Me iPr Ib55 CFCl₂Me iPr Ib56 CCl₃ Me iPr Ib57 OCF₃ Me iPr Ib58 OCHF₂ Me iPr Ib59 OCF₂CF₃Me iPr Ib60 OCF₂CHF₂ Me iPr Ib61 OCF(CF₃)₂ Me iPr Ib62 OCF₂Cl Me iPrIb63 OCFCl₂ Me iPr Ib64 OCCl₃ Me iPr Ib65 CF₃ Me Bu Ib66 CHF₂ Me Bu Ib67CF₂CF₃ Me Bu Ib68 CF(CF₃)₂ Me Bu Ib69 COH(CF₃)₂ Me Bu Ib70 CF₂Cl Me BuIb71 CFCl₂ Me Bu Ib72 CCl₃ Me Bu Ib73 OCF₃ Me Bu Ib74 OCHF₂ Me Bu Ib75OCF₂CF₃ Me Bu Ib76 OCF₂CHF₂ Me Bu Ib77 OCF(CF₃)₂ Me Bu Ib78 OCF₂Cl Me BuIb79 OCFCl₂ Me Bu Ib80 OCCl₃ Me Bu Ib81 CF₃ Me Pn Ib82 CHF₂ Me Pn Ib83CF₂CF₃ Me Pn Ib84 CF(CF₃)₂ Me Pn Ib85 COH(CF₃)₂ Me Pn Ib86 CF₂Cl Me PnIb87 CFCl₂ Me Pn Ib88 CCl₃ Me Pn Ib89 OCF₃ Me Pn Ib90 OCHF₂ Me Pn Ib91OCF₂CF₃ Me Pn Ib92 OCF₂CHF₂ Me Pn Ib93 OCF(CF₃)₂ Me Pn Ib94 OCF₂Cl Me PnIb95 OCFCl₂ Me Pn Ib96 OCCl₃ Me Pn Ib97 CF₃ Me Me—cPr Ib98 CHF₂ MeMe—cPr Ib99 CF₂CF₃ Me Me—cPr Ib100 CF(CF₃)₂ Me Me—cPr Ib101 COH(CF₃)₂ MeMe—cPr Ib102 CF₂Cl Me Me—cPr Ib103 CFCl₂ Me Me—cPr Ib104 CCl₃ Me Me—cPrIb105 OCF₃ Me Me—cPr Ib106 OCHF₂ Me Me—cPr Ib107 OCF₂CF₃ Me Me—cPr Ib108OCF₂CHF₂ Me Me—cPr Ib109 OCF(CF3)2 Me Me—cPr Ib110 OCF₂Cl Me Me—cPrIb111 OCFCl₂ Me Me—cPr Ib112 OCCl₃ Me Me—cPr Ib113 CF₃ Me allyl Ib114CHF₂ Me allyl Ib115 CF₂CF₃ Me allyl Ib116 CF(CF₃)₂ Me allyl Ib117COH(CF₃)₂ Me allyl Ib118 CF₂Cl Me allyl Ib119 CFCl₂ Me allyl Ib120 CCl₃Me allyl Ib121 OCF₃ Me allyl Ib122 OCHF₂ Me allyl Ib123 OCF₂CF₃ Me allylIb124 OCF₂CHF₂ Me allyl Ib125 OCF(CF₃)₂ Me allyl Ib126 OCF₂Cl Me allylIb127 OCFCl₂ Me allyl Ib128 OCCl₃ Me allyl Ib129 CF₃ Me propargyl Ib130CHF₂ Me propargyl Ib131 CF₂CF₃ Me propargyl Ib132 CF(CF₃)₂ Me propargylIb133 COH(CF₃)₂ Me propargyl Ib134 CF₂Cl Me propargyl Ib135 CFCl₂ Mepropargyl Ib136 CCl₃ Me propargyl Ib137 OCF₃ Me propargyl Ib138 OCHF₂ Mepropargyl Ib139 OCF₂CF₃ Me propargyl Ib140 OCF₂CHF₂ Me propargyl Ib141OCF(CF₃)₂ Me propargyl Ib142 OCF₂Cl Me propargyl Ib143 OCFCl₂ Mepropargyl Ib144 OCCl₃ Me propargyl Ib145 CF₃ Me Me—CN Ib146 CHF₂ MeMe—CN Ib147 CF₂CF₃ Me Me—CN Ib148 CF(CF₃)₂ Me Me—CN Ib149 COH(CF₃)₂ MeMe—CN Ib150 CF₂Cl Me Me—CN Ib151 CFCl₂ Me Me—CN Ib152 CCl₃ Me Me—CNIb153 OCF₃ Me Me—CN Ib154 OCHF₂ Me Me—CN Ib155 OCF₂CF₃ Me Me—CN Ib156OCF₂CHF₂ Me Me—CN Ib157 OCF(CF₃)₂ Me Me—CN Ib158 OCF₂Cl Me Me—CN Ib159OCFCl₂ Me Me—CN Ib160 OCCl₃ Me Me—CN Ib161 CF₃ Et Et Ib162 CHF₂ Et EtIb163 CF₂CF₃ Et Et Ib164 CF(CF₃)₂ Et Et Ib165 COH(CF₃)₂ Et Et Ib166CF₂Cl Et Et Ib167 CFCl₂ Et Et Ib168 CCl₃ Et Et Ib169 OCF₃ Et Et Ib170OCHF₂ Et Et Ib171 OCF₂CF₃ Et Et Ib172 OCF₂CHF₂ Et Et Ib173 OCF(CF₃)₂ EtEt Ib174 OCF₂Cl Et Et Ib175 OCFCl₂ Et Et Ib176 OCCl₃ Et Et Ib177 CF₃ EtPr Ib178 CHF₂ Et Pr Ib179 CF₂CF₃ Et Pr Ib180 CF(CF₃)₂ Et Pr Ib181COH(CF₃)₂ Et Pr Ib182 CF₂Cl Et Pr Ib183 CFCl₂ Et Pr Ib184 CCl₃ Et PrIb185 OCF₃ Et Pr Ib186 OCHF₂ Et Pr Ib187 OCF₂CF₃ Et Pr Ib188 OCF₂CHF₂ EtPr Ib189 OCF(CF3)2 Et Pr Ib190 OCF₂Cl Et Pr Ib191 OCFCl₂ Et Pr Ib192OCCl₃ Et Pr Ib193 CF₃ Et iPr Ib194 CHF₂ Et iPr Ib195 CF₂CF₃ Et iPr Ib196CF(CF₃)₂ Et iPr Ib197 COH(CF₃)₂ Et iPr Ib198 CF₂Cl Et iPr Ib199 CFCl₂ EtiPr Ib200 CCl₃ Et iPr Ib201 OCF₃ Et iPr Ib202 OCHF₂ Et iPr Ib203 OCF₂CF₃Et iPr Ib204 OCF₂CHF₂ Et iPr Ib205 OCF(CF₃)₂ Et iPr Ib206 OCF₂Cl Et iPrIb207 OCFCl₂ Et iPr Ib208 OCCl₃ Et iPr Ib209 CF₃ Et Bu Ib210 CHF₂ Et BuIb211 CF₂CF₃ Et Bu Ib212 CF(CF₃)₂ Et Bu Ib213 COH(CF₃)₂ Et Bu Ib214CF₂Cl Et Bu Ib215 CFCl₂ Et Bu Ib216 CCl₃ Et Bu Ib217 OCF₃ Et Bu Ib218OCHF₂ Et Bu Ib219 OCF₂CF₃ Et Bu Ib220 OCF₂CHF₂ Et Bu Ib221 OCF(CF₃)₂ EtBu Ib222 OCF₂Cl Et Bu Ib223 OCFCl₂ Et Bu Ib224 OCCl₃ Et Bu Ib225 CF₃ EtPn Ib226 CHF₂ Et Pn Ib227 CF₂CF₃ Et Pn Ib228 CF(CF₃)₂ Et Pn Ib229COH(CF₃)₂ Et Pn Ib230 CF₂Cl Et Pn Ib231 CFCl₂ Et Pn Ib232 CCl₃ Et PnIb233 OCF₃ Et Pn Ib234 OCHF₂ Et Pn Ib235 OCF₂CF₃ Et Pn Ib236 OCF₂CHF₂ EtPn Ib237 OCF(CF₃)₂ Et Pn Ib238 OCF₂Cl Et Pn Ib239 OCFCl₂ Et Pn Ib240OCCl₃ Et Pn Ib241 CF₃ Et Me—cPr Ib242 CHF₂ Et Me—cPr Ib243 CF₂CF₃ EtMe—cPr Ib244 CF(CF₃)₂ Et Me—cPr Ib245 COH(CF₃)₂ Et Me—cPr Ib246 CF₂Cl EtMe—cPr Ib247 CFCl₂ Et Me—cPr Ib248 CCl₃ Et Me—cPr Ib249 OCF₃ Et Me—cPrIb250 OCHF₂ Et Me—cPr Ib251 OCF₂CF₃ Et Me—cPr Ib252 OCF₂CHF₂ Et Me—cPrIb253 OCF(CF3)2 Et Me—cPr Ib254 OCF₂Cl Et Me—cPr Ib255 OCFCl₂ Et Me—cPrIb256 OCCl₃ Et Me—cPr Ib257 CF₃ Et allyl Ib258 CHF₂ Et allyl Ib259CF₂CF₃ Et allyl Ib260 CF(CF₃)₂ Et allyl Ib261 COH(CF₃)₂ Et allyl Ib262CF₂Cl Et allyl Ib263 CFCl₂ Et allyl Ib264 CCl₃ Et allyl Ib265 OCF₃ Etallyl Ib266 OCHF₂ Et allyl Ib267 OCF₂CF₃ Et allyl Ib268 OCF₂CHF₂ Etallyl Ib269 OCF(CF₃)₂ Et allyl Ib270 OCF₂Cl Et allyl Ib271 OCFCl₂ Etallyl Ib272 OCCl₃ Et allyl Ib273 CF₃ Et propargyl Ib274 CHF₂ Etpropargyl Ib275 CF₂CF₃ Et propargyl Ib276 CF(CF₃)₂ Et propargyl Ib277COH(CF₃)₂ Et propargyl Ib278 CF₂Cl Et propargyl Ib279 CFCl₂ Et propargylIb280 CCl₃ Et propargyl Ib281 OCF₃ Et propargyl Ib282 OCHF₂ Et propargylIb283 OCF₂CF₃ Et propargyl Ib284 OCF₂CHF₂ Et propargyl Ib285 OCF(CF₃)₂Et propargyl Ib286 OCF₂Cl Et propargyl Ib287 OCFCl₂ Et propargyl Ib288OCCl₃ Et propargyl Ib289 CF₃ Et Me—CN Ib290 CHF₂ Et Me—CN Ib291 CF₂CF₃Et Me—CN Ib292 CF(CF₃)₂ Et Me—CN Ib293 COH(CF₃)₂ Et Me—CN Ib294 CF₂Cl EtMe—CN Ib295 CFCl₂ Et Me—CN Ib296 CCl₃ Et Me—CN Ib297 OCF₃ Et Me—CN Ib298OCHF₂ Et Me—CN Ib299 OCF₂CF₃ Et Me—CN Ib300 OCF₂CHF₂ Et Me—CN Ib301OCF(CF₃)₂ Et Me—CN Ib302 OCF₂Cl Et Me—CN Ib303 OCFCl₂ Et Me—CN Ib304OCCl₃ Et Me—CN Ib305 CF₃ Pr Pr Ib306 CHF₂ Pr Pr Ib307 CF₂CF₃ Pr Pr Ib308CF(CF₃)₂ Pr Pr Ib309 COH(CF₃)₂ Pr Pr Ib310 CF₂Cl Pr Pr Ib311 CFCl₂ Pr PrIb312 CCl₃ Pr Pr Ib313 OCF₃ Pr Pr Ib314 OCHF₂ Pr Pr Ib315 OCF₂CF₃ Pr PrIb316 OCF₂CHF₂ Pr Pr Ib317 OCF(CF3)2 Pr Pr Ib318 OCF₂Cl Pr Pr Ib319OCFCl₂ Pr Pr Ib320 OCCl₃ Pr Pr Ib321 CF₃ Pr iPr Ib322 CHF₂ Pr iPr Ib323CF₂CF₃ Pr iPr Ib324 CF(CF₃)₂ Pr iPr Ib325 COH(CF₃)₂ Pr iPr Ib326 CF₂ClPr iPr Ib327 CFCl₂ Pr iPr Ib328 CCl₃ Pr iPr Ib329 OCF₃ Pr iPr Ib330OCHF₂ Pr iPr Ib331 OCF₂CF₃ Pr iPr Ib332 OCF₂CHF₂ Pr iPr Ib333 OCF(CF₃)₂Pr iPr Ib334 OCF₂Cl Pr iPr Ib335 OCFCl₂ Pr iPr Ib336 OCCl₃ Pr iPr Ib337CF₃ Pr Bu Ib338 CHF₂ Pr Bu Ib339 CF₂CF₃ Pr Bu Ib340 CF(CF₃)₂ Pr Bu Ib341COH(CF₃)₂ Pr Bu Ib342 CF₂Cl Pr Bu Ib343 CFCl₂ Pr Bu Ib344 CCl₃ Pr BuIb345 OCF₃ Pr Bu Ib346 OCHF₂ Pr Bu Ib347 OCF₂CF₃ Pr Bu Ib348 OCF₂CHF₂ PrBu Ib349 OCF(CF₃)₂ Pr Bu Ib350 OCF₂Cl Pr Bu Ib351 OCFCl₂ Pr Bu Ib352OCCl₃ Pr Bu Ib353 CF₃ Pr Pn Ib354 CHF₂ Pr Pn Ib355 CF₂CF₃ Pr Pn Ib356CF(CF₃)₂ Pr Pn Ib357 COH(CF₃)₂ Pr Pn Ib358 CF₂Cl Pr Pn Ib359 CFCl₂ Pr PnIb360 CCl₃ Pr Pn Ib361 OCF₃ Pr Pn Ib362 OCHF₂ Pr Pn Ib363 OCF₂CF₃ Pr PnIb364 OCF₂CHF₂ Pr Pn Ib365 OCF(CF₃)₂ Pr Pn Ib366 OCF₂Cl Pr Pn Ib367OCFCl₂ Pr Pn Ib368 OCCl₃ Pr Pn Ib369 CF₃ Pr Me—cPr Ib370 CHF₂ Pr Me—cPrIb371 CF₂CF₃ Pr Me—cPr Ib372 CF(CF₃)₂ Pr Me—cPr Ib373 COH(CF₃)₂ PrMe—cPr Ib374 CF₂Cl Pr Me—cPr Ib375 CFCl₂ Pr Me—cPr Ib376 CCl₃ Pr Me—cPrIb377 OCF₃ Pr Me—cPr Ib378 OCHF₂ Pr Me—cPr Ib379 OCF₂CF₃ Pr Me—cPr Ib380OCF₂CHF₂ Pr Me—cPr Ib381 OCF(CF3)2 Pr Me—cPr Ib382 OCF₂Cl Pr Me—cPrIb383 OCFCl₂ Pr Me—cPr Ib384 OCCl₃ Pr Me—cPr Ib385 CF₃ Pr allyl Ib386CHF₂ Pr allyl Ib387 CF₂CF₃ Pr allyl Ib388 CF(CF₃)₂ Pr allyl Ib389COH(CF₃)₂ Pr allyl Ib390 CF₂Cl Pr allyl Ib391 CFCl₂ Pr allyl Ib392 CCl₃Pr allyl Ib393 OCF₃ Pr allyl Ib394 OCHF₂ Pr allyl Ib395 OCF₂CF₃ Pr allylIb396 OCF₂CHF₂ Pr allyl Ib397 OCF(CF₃)₂ Pr allyl Ib398 OCF₂Cl Pr allylIb399 OCFCl₂ Pr allyl Ib400 OCCl₃ Pr allyl Ib401 CF₃ Pr propargyl Ib402CHF₂ Pr propargyl Ib403 CF₂CF₃ Pr propargyl Ib404 CF(CF₃)₂ Pr propargylIb405 COH(CF₃)₂ Pr propargyl Ib406 CF₂Cl Pr propargyl Ib407 CFCl₂ Prpropargyl Ib408 CCl₃ Pr propargyl Ib409 OCF₃ Pr propargyl Ib410 OCHF₂ Prpropargyl Ib411 OCF₂CF₃ Pr propargyl Ib412 OCF₂CHF₂ Pr propargyl Ib413OCF(CF₃)₂ Pr propargyl Ib414 OCF₂Cl Pr propargyl Ib415 OCFCl₂ Prpropargyl Ib416 OCCl₃ Pr propargyl Ib417 CF₃ Pr Me—CN Ib418 CHF₂ PrMe—CN Ib419 CF₂CF₃ Pr Me—CN Ib420 CF(CF₃)₂ Pr Me—CN Ib421 COH(CF₃)₂ PrMe—CN Ib422 CF₂Cl Pr Me—CN Ib423 CFCl₂ Pr Me—CN Ib424 CCl₃ Pr Me—CNIb425 OCF₃ Pr Me—CN Ib426 OCHF₂ Pr Me—CN Ib427 OCF₂CF₃ Pr Me—CN Ib428OCF₂CHF₂ Pr Me—CN Ib429 OCF(CF₃)₂ Pr Me—CN Ib430 OCF₂Cl Pr Me—CN Ib431OCFCl₂ Pr Me—CN Ib432 OCCl₃ Pr Me—CN Ib433 CF₃ Pr Pr Ib434 CHF₂ Pr PrIb435 CF₂CF₃ Pr Pr Ib436 CF(CF₃)₂ Pr Pr Ib437 COH(CF₃)₂ Pr Pr Ib438CF₂Cl Pr Pr Ib439 CFCl₂ Pr Pr Ib440 CCl₃ Pr Pr Ib441 OCF₃ Pr Pr Ib442OCHF₂ Pr Pr Ib443 OCF₂CF₃ Pr Pr Ib444 OCF₂CHF₂ Pr Pr Ib445 OCF(CF3)2 PrPr Ib446 OCF₂Cl Pr Pr Ib447 OCFCl₂ Pr Pr Ib448 OCCl₃ Pr Pr Ib449 CF₃ PriPr Ib450 CHF₂ Pr iPr Ib451 CF₂CF₃ Pr iPr Ib452 CF(CF₃)₂ Pr iPr Ib453COH(CF₃)₂ Pr iPr Ib454 CF₂Cl Pr iPr Ib455 CFCl₂ Pr iPr Ib456 CCl₃ Pr iPrIb457 OCF₃ Pr iPr Ib458 OCHF₂ Pr iPr Ib459 OCF₂CF₃ Pr iPr Ib460 OCF₂CHF₂Pr iPr Ib461 OCF(CF₃)₂ Pr iPr Ib462 OCF₂Cl Pr iPr Ib463 OCFCl₂ Pr iPrIb464 OCCl₃ Pr iPr Ib465 CF₃ Pr Bu Ib466 CHF₂ Pr Bu Ib467 CF₂CF₃ Pr BuIb468 CF(CF₃)₂ Pr Bu Ib469 COH(CF₃)₂ Pr Bu Ib470 CF₂Cl Pr Bu Ib471 CFCl₂Pr Bu Ib472 CCl₃ Pr Bu Ib473 OCF₃ Pr Bu Ib474 OCHF₂ Pr Bu Ib475 OCF₂CF₃Pr Bu Ib476 OCF₂CHF₂ Pr Bu Ib477 OCF(CF₃)₂ Pr Bu Ib478 OCF₂Cl Pr BuIb479 OCFCl₂ Pr Bu Ib480 OCCl₃ Pr Bu Ib481 CF₃ Pr Pn Ib482 CHF₂ Pr PnIb483 CF₂CF₃ Pr Pn Ib484 CF(CF₃)₂ Pr Pn Ib485 COH(CF₃)₂ Pr Pn Ib486CF₂Cl Pr Pn Ib487 CFCl₂ Pr Pn Ib488 CCl₃ Pr Pn Ib489 OCF₃ Pr Pn Ib490OCHF₂ Pr Pn Ib491 OCF₂CF₃ Pr Pn Ib492 OCF₂CHF₂ Pr Pn Ib493 OCF(CF₃)₂ PrPn Ib494 OCF₂Cl Pr Pn Ib495 OCFCl₂ Pr Pn Ib496 OCCl₃ Pr Pn Ib497 CF₃ PrMe—cPr Ib498 CHF₂ Pr Me—cPr Ib499 CF₂CF₃ Pr Me—cPr Ib500 CF(CF₃)₂ PrMe—cPr Ib501 COH(CF₃)₂ Pr Me—cPr Ib502 CF₂Cl Pr Me—cPr Ib503 CFCl₂ PrMe—cPr Ib504 CCl₃ Pr Me—cPr Ib505 OCF₃ Pr Me—cPr Ib506 OCHF₂ Pr Me—cPrIb507 OCF₂CF₃ Pr Me—cPr Ib508 OCF₂CHF₂ Pr Me—cPr Ib509 OCF(CF3)2 PrMe—cPr Ib510 OCF₂Cl Pr Me—cPr Ib511 OCFCl₂ Pr Me—cPr Ib512 OCCl₃ PrMe—cPr Ib513 CF₃ Pr allyl Ib514 CHF₂ Pr allyl Ib515 CF₂CF₃ Pr allylIb516 CF(CF₃)₂ Pr allyl Ib517 COH(CF₃)₂ Pr allyl Ib518 CF₂Cl Pr allylIb519 CFCl₂ Pr allyl Ib520 CCl₃ Pr allyl Ib521 OCF₃ Pr allyl Ib522 OCHF₂Pr allyl Ib523 OCF₂CF₃ Pr allyl Ib524 OCF₂CHF₂ Pr allyl Ib525 OCF(CF₃)₂Pr allyl Ib526 OCF₂Cl Pr allyl Ib527 OCFCl₂ Pr allyl Ib528 OCCl₃ Prallyl Ib529 CF₃ Pr propargyl Ib530 CHF₂ Pr propargyl Ib531 CF₂CF₃ Prpropargyl Ib532 CF(CF₃)₂ Pr propargyl Ib533 COH(CF₃)₂ Pr propargyl Ib534CF₂Cl Pr propargyl Ib535 CFCl₂ Pr propargyl Ib536 CCl₃ Pr propargylIb537 OCF₃ Pr propargyl Ib538 OCHF₂ Pr propargyl Ib539 OCF₂CF₃ Prpropargyl Ib540 OCF₂CHF₂ Pr propargyl Ib541 OCF(CF₃)₂ Pr propargyl Ib542OCF₂Cl Pr propargyl Ib543 OCFCl₂ Pr propargyl Ib544 OCCl₃ Pr propargylIb545 CF₃ Pr Me—CN Ib546 CHF₂ Pr Me—CN Ib547 CF₂CF₃ Pr Me—CN Ib548CF(CF₃)₂ Pr Me—CN Ib549 COH(CF₃)₂ Pr Me—CN Ib550 CF₂Cl Pr Me—CN Ib551CFCl₂ Pr Me—CN Ib552 CCl₃ Pr Me—CN Ib553 OCF₃ Pr Me—CN Ib554 OCHF₂ PrMe—CN Ib555 OCF₂CF₃ Pr Me—CN Ib556 OCF₂CHF₂ Pr Me—CN Ib557 OCF(CF₃)₂ PrMe—CN Ib558 OCF₂Cl Pr Me—CN Ib559 OCFCl₂ Pr Me—CN Ib560 OCCl₃ Pr Me—CNIb561 CF₃ iPr iPr Ib562 CHF₂ iPr iPr Ib563 CF₂CF₃ iPr iPr Ib564 CF(CF₃)₂iPr iPr Ib565 COH(CF₃)₂ iPr iPr Ib566 CF₂Cl iPr iPr Ib567 CFCl₂ iPr iPrIb568 CCl₃ iPr iPr Ib569 OCF₃ iPr iPr Ib570 OCHF₂ iPr iPr Ib571 OCF₂CF₃iPr iPr Ib572 OCF₂CHF₂ iPr iPr Ib573 OCF(CF₃)₂ iPr iPr Ib574 OCF₂Cl iPriPr Ib575 OCFCl₂ iPr iPr Ib576 OCCl₃ iPr iPr Ib577 CF₃ iPr Bu Ib578 CHF₂iPr Bu Ib579 CF₂CF₃ iPr Bu Ib580 CF(CF₃)₂ iPr Bu Ib581 COH(CF₃)₂ iPr BuIb582 CF₂Cl iPr Bu Ib583 CFCl₂ iPr Bu Ib584 CCl₃ iPr Bu Ib585 OCF₃ iPrBu Ib586 OCHF₂ iPr Bu Ib587 OCF₂CF₃ iPr Bu Ib588 OCF₂CHF₂ iPr Bu Ib589OCF(CF₃)₂ iPr Bu Ib590 OCF₂Cl iPr Bu Ib591 OCFCl₂ iPr Bu Ib592 OCCl₃ iPrBu Ib593 CF₃ iPr Pn Ib594 CHF₂ iPr Pn Ib595 CF₂CF₃ iPr Pn Ib596 CF(CF₃)₂iPr Pn Ib597 COH(CF₃)₂ iPr Pn Ib598 CF₂Cl iPr Pn Ib599 CFCl₂ iPr PnIb600 CCl₃ iPr Pn Ib601 OCF₃ iPr Pn Ib602 OCHF₂ iPr Pn Ib603 OCF₂CF₃ iPrPn Ib604 OCF₂CHF₂ iPr Pn Ib605 OCF(CF₃)₂ iPr Pn Ib606 OCF₂Cl iPr PnIb607 OCFCl₂ iPr Pn Ib608 OCCl₃ iPr Pn Ib609 CF₃ iPr Me—cPr Ib610 CHF₂iPr Me—cPr Ib611 CF₂CF₃ iPr Me—cPr Ib612 CF(CF₃)₂ iPr Me—cPr Ib613COH(CF₃)₂ iPr Me—cPr Ib614 CF₂Cl iPr Me—cPr Ib615 CFCl₂ iPr Me—cPr Ib616CCl₃ iPr Me—cPr Ib617 OCF₃ iPr Me—cPr Ib618 OCHF₂ iPr Me—cPr Ib619OCF₂CF₃ iPr Me—cPr Ib620 OCF₂CHF₂ iPr Me—cPr Ib621 OCF(CF3)2 iPr Me—cPrIb622 OCF₂Cl iPr Me—cPr Ib623 OCFCl₂ iPr Me—cPr Ib624 OCCl₃ iPr Me—cPrIb625 CF₃ iPr allyl Ib626 CHF₂ iPr allyl Ib627 CF₂CF₃ iPr allyl Ib628CF(CF₃)₂ iPr allyl Ib629 COH(CF₃)₂ iPr allyl Ib630 CF₂Cl iPr allyl Ib631CFCl₂ iPr allyl Ib632 CCl₃ iPr allyl Ib633 OCF₃ iPr allyl Ib634 OCHF₂iPr allyl Ib635 OCF₂CF₃ iPr allyl Ib636 OCF₂CHF₂ iPr allyl Ib637OCF(CF₃)₂ iPr allyl Ib638 OCF₂Cl iPr allyl Ib639 OCFCl₂ iPr allyl Ib640OCCl₃ iPr allyl Ib641 CF₃ iPr propargyl Ib642 CHF₂ iPr propargyl Ib643CF₂CF₃ iPr propargyl Ib644 CF(CF₃)₂ iPr propargyl Ib645 COH(CF₃)₂ iPrpropargyl Ib646 CF₂Cl iPr propargyl Ib647 CFCl₂ iPr propargyl Ib648 CCl₃iPr propargyl Ib649 OCF₃ iPr propargyl Ib650 OCHF₂ iPr propargyl Ib651OCF₂CF₃ iPr propargyl Ib652 OCF₂CHF₂ iPr propargyl Ib653 OCF(CF₃)₂ iPrpropargyl Ib654 OCF₂Cl iPr propargyl Ib655 OCFCl₂ iPr propargyl Ib656OCCl₃ iPr propargyl Ib657 CF₃ iPr Me—CN Ib658 CHF₂ iPr Me—CN Ib659CF₂CF₃ iPr Me—CN Ib660 CF(CF₃)₂ iPr Me—CN Ib661 COH(CF₃)₂ iPr Me—CNIb662 CF₂Cl iPr Me—CN Ib663 CFCl₂ iPr Me—CN Ib664 CCl₃ iPr Me—CN Ib665OCF₃ iPr Me—CN Ib666 OCHF₂ iPr Me—CN Ib667 OCF₂CF₃ iPr Me—CN Ib668OCF₂CHF₂ iPr Me—CN Ib669 OCF(CF₃)₂ iPr Me—CN Ib670 OCF₂Cl iPr Me—CNIb671 OCFCl₂ iPr Me—CN Ib672 OCCl₃ iPr Me—CN Ib673 CF₃ Bu Bu Ib674 CHF₂Bu Bu Ib675 CF₂CF₃ Bu Bu Ib676 CF(CF₃)₂ Bu Bu Ib677 COH(CF₃)₂ Bu BuIb678 CF₂Cl Bu Bu Ib679 CFCl₂ Bu Bu Ib680 CCl₃ Bu Bu Ib681 OCF₃ Bu BuIb682 OCHF₂ Bu Bu Ib683 OCF₂CF₃ Bu Bu Ib684 OCF₂CHF₂ Bu Bu Ib685OCF(CF₃)₂ Bu Bu Ib686 OCF₂Cl Bu Bu Ib687 OCFCl₂ Bu Bu Ib688 OCCl₃ Bu BuIb689 CF₃ Bu Pn Ib690 CHF₂ Bu Pn Ib691 CF₂CF₃ Bu Pn Ib692 CF(CF₃)₂ Bu PnIb693 COH(CF₃)₂ Bu Pn Ib694 CF₂Cl Bu Pn Ib695 CFCl₂ Bu Pn Ib696 CCl₃ BuPn Ib697 OCF₃ Bu Pn Ib698 OCHF₂ Bu Pn Ib699 OCF₂CF₃ Bu Pn Ib700 OCF₂CHF₂Bu Pn Ib701 OCF(CF₃)₂ Bu Pn Ib702 OCF₂Cl Bu Pn Ib703 OCFCl₂ Bu Pn Ib704OCCl₃ Bu Pn Ib705 CF₃ Bu Me—cPr Ib706 CHF₂ Bu Me—cPr Ib707 CF₂CF₃ BuMe—cPr Ib708 CF(CF₃)₂ Bu Me—cPr Ib709 COH(CF₃)₂ Bu Me—cPr Ib710 CF₂Cl BuMe—cPr Ib711 CFCl₂ Bu Me—cPr Ib712 CCl₃ Bu Me—cPr Ib713 OCF₃ Bu Me—cPrIb714 OCHF₂ Bu Me—cPr Ib715 OCF₂CF₃ Bu Me—cPr Ib716 OCF₂CHF₂ Bu Me—cPrIb717 OCF(CF3)2 Bu Me—cPr Ib718 OCF₂Cl Bu Me—cPr Ib719 OCFCl₂ Bu Me—cPrIb720 OCCl₃ Bu Me—cPr Ib721 CF₃ Bu allyl Ib722 CHF₂ Bu allyl Ib723CF₂CF₃ Bu allyl Ib724 CF(CF₃)₂ Bu allyl Ib725 COH(CF₃)₂ Bu allyl Ib726CF₂Cl Bu allyl Ib727 CFCl₂ Bu allyl Ib728 CCl₃ Bu allyl Ib729 OCF₃ Buallyl Ib730 OCHF₂ Bu allyl Ib731 OCF₂CF₃ Bu allyl Ib732 OCF₂CHF₂ Buallyl Ib733 OCF(CF₃)₂ Bu allyl Ib734 OCF₂Cl Bu allyl Ib735 OCFCl₂ Buallyl Ib736 OCCl₃ Bu allyl Ib737 CF₃ Bu propargyl Ib738 CHF₂ Bupropargyl Ib739 CF₂CF₃ Bu propargyl Ib740 CF(CF₃)₂ Bu propargyl Ib741COH(CF₃)₂ Bu propargyl Ib742 CF₂Cl Bu propargyl Ib743 CFCl₂ Bu propargylIb744 CCl₃ Bu propargyl Ib745 OCF₃ Bu propargyl Ib746 OCHF₂ Bu propargylIb747 OCF₂CF₃ Bu propargyl Ib748 OCF₂CHF₂ Bu propargyl Ib749 OCF(CF₃)₂Bu propargyl Ib750 OCF₂Cl Bu propargyl Ib751 OCFCl₂ Bu propargyl Ib752OCCl₃ Bu propargyl Ib753 CF₃ Bu Me—CN Ib754 CHF₂ Bu Me—CN Ib755 CF₂CF₃Bu Me—CN Ib756 CF(CF₃)₂ Bu Me—CN Ib757 COH(CF₃)₂ Bu Me—CN Ib758 CF₂Cl BuMe—CN Ib759 CFCl₂ Bu Me—CN Ib760 CCl₃ Bu Me—CN Ib761 OCF₃ Bu Me—CN Ib762OCHF₂ Bu Me—CN Ib763 OCF₂CF₃ Bu Me—CN Ib764 OCF₂CHF₂ Bu Me—CN Ib765OCF(CF₃)₂ Bu Me—CN Ib766 OCF₂Cl Bu Me—CN Ib767 OCFCl₂ Bu Me—CN Ib768OCCl₃ Bu Me—CN Ib769 CF₃ Pn Pn Ib770 CHF₂ Pn Pn Ib771 CF₂CF₃ Pn Pn Ib772CF(CF₃)₂ Pn Pn Ib773 COH(CF₃)₂ Pn Pn Ib774 CF₂Cl Pn Pn Ib775 CFCl₂ Pn PnIb776 CCl₃ Pn Pn Ib777 OCF₃ Pn Pn Ib778 OCHF₂ Pn Pn Ib779 OCF₂CF₃ Pn PnIb780 OCF₂CHF₂ Pn Pn Ib781 OCF(CF₃)₂ Pn Pn Ib782 OCF₂Cl Pn Pn Ib783OCFCl₂ Pn Pn Ib784 OCCl₃ Pn Pn Ib785 CF₃ Pn Me—cPr Ib786 CHF₂ Pn Me—cPrIb787 CF₂CF₃ Pn Me—cPr Ib788 CF(CF₃)₂ Pn Me—cPr Ib789 COH(CF₃)₂ PnMe—cPr Ib790 CF₂Cl Pn Me—cPr Ib791 CFCl₂ Pn Me—cPr Ib792 CCl₃ Pn Me—cPrIb793 OCF₃ Pn Me—cPr Ib794 OCHF₂ Pn Me—cPr Ib795 OCF₂CF₃ Pn Me—cPr Ib796OCF₂CHF₂ Pn Me—cPr Ib797 OCF(CF3)2 Pn Me—cPr Ib798 OCF₂Cl Pn Me—cPrIb799 OCFCl₂ Pn Me—cPr Ib800 OCCl₃ Pn Me—cPr Ib801 CF₃ Pn allyl Ib802CHF₂ Pn allyl Ib803 CF₂CF₃ Pn allyl Ib804 CF(CF₃)₂ Pn allyl Ib805COH(CF₃)₂ Pn allyl Ib806 CF₂Cl Pn allyl Ib807 CFCl₂ Pn allyl Ib808 CCl₃Pn allyl Ib809 OCF₃ Pn allyl Ib810 OCHF₂ Pn allyl Ib811 OCF₂CF₃ Pn allylIb812 OCF₂CHF₂ Pn allyl Ib813 OCF(CF₃)₂ Pn allyl Ib814 OCF₂Cl Pn allylIb815 OCFCl₂ Pn allyl Ib816 OCCl₃ Pn allyl Ib817 CF₃ Pn propargyl Ib818CHF₂ Pn propargyl Ib819 CF₂CF₃ Pn propargyl Ib820 CF(CF₃)₂ Pn propargylIb821 COH(CF₃)₂ Pn propargyl Ib822 CF₂Cl Pn propargyl Ib823 CFCl₂ Pnpropargyl Ib824 CCl₃ Pn propargyl Ib825 OCF₃ Pn propargyl Ib826 OCHF₂ Pnpropargyl Ib827 OCF₂CF₃ Pn propargyl Ib828 OCF₂CHF₂ Pn propargyl Ib829OCF(CF₃)₂ Pn propargyl Ib830 OCF₂Cl Pn propargyl Ib831 OCFCl₂ Pnpropargyl Ib832 OCCl₃ Pn propargyl Ib833 CF₃ Pn Me—CN Ib834 CHF₂ PnMe—CN Ib835 CF₂CF₃ Pn Me—CN Ib836 CF(CF₃)₂ Pn Me—CN Ib837 COH(CF₃)₂ PnMe—CN Ib838 CF₂Cl Pn Me—CN Ib839 CFCl₂ Pn Me—CN Ib840 CCl₃ Pn Me—CNIb841 OCF₃ Pn Me—CN Ib842 OCHF₂ Pn Me—CN Ib843 OCF₂CF₃ Pn Me—CN Ib844OCF₂CHF₂ Pn Me—CN Ib845 OCF(CF₃)₂ Pn Me—CN Ib846 OCF₂Cl Pn Me—CN Ib847OCFCl₂ Pn Me—CN Ib848 OCCl₃ Pn Me—CN Ib849 CF₃ Me—cPr Me—cPr Ib850 CHF₂Me—cPr Me—cPr Ib851 CF₂CF₃ Me—cPr Me—cPr Ib852 CF(CF₃)₂ Me—cPr Me—cPrIb853 COH(CF₃)₂ Me—cPr Me—cPr Ib854 CF₂Cl Me—cPr Me—cPr Ib855 CFCl₂Me—cPr Me—cPr Ib856 CCl₃ Me—cPr Me—cPr Ib857 OCF₃ Me—cPr Me—cPr Ib858OCHF₂ Me—cPr Me—cPr Ib859 OCF₂CF₃ Me—cPr Me—cPr Ib860 OCF₂CHF₂ Me—cPrMe—cPr Ib861 OCF(CF3)2 Me—cPr Me—cPr Ib862 OCF₂Cl Me—cPr Me—cPr Ib863OCFCl₂ Me—cPr Me—cPr Ib864 OCCl₃ Me—cPr Me—cPr Ib865 CF₃ Me—cPr allylIb866 CHF₂ Me—cPr allyl Ib867 CF₂CF₃ Me—cPr allyl Ib868 CF(CF₃)₂ Me—cPrallyl Ib869 COH(CF₃)₂ Me—cPr allyl Ib870 CF₂Cl Me—cPr allyl Ib871 CFCl₂Me—cPr allyl Ib872 CCl₃ Me—cPr allyl Ib873 OCF₃ Me—cPr allyl Ib874 OCHF₂Me—cPr allyl Ib875 OCF₂CF₃ Me—cPr allyl Ib876 OCF₂CHF₂ Me—cPr allylIb877 OCF(CF₃)₂ Me—cPr allyl Ib878 OCF₂Cl Me—cPr allyl Ib879 OCFCl₂Me—cPr allyl Ib880 OCCl₃ Me—cPr allyl Ib881 CF₃ Me—cPr propargyl Ib882CHF₂ Me—cPr propargyl Ib883 CF₂CF₃ Me—cPr propargyl Ib884 CF(CF₃)₂Me—cPr propargyl Ib885 COH(CF₃)₂ Me—cPr propargyl Ib886 CF₂Cl Me—cPrpropargyl Ib887 CFCl₂ Me—cPr propargyl Ib888 CCl₃ Me—cPr propargyl Ib889OCF₃ Me—cPr propargyl Ib890 OCHF₂ Me—cPr propargyl Ib891 OCF₂CF₃ Me—cPrpropargyl Ib892 OCF₂CHF₂ Me—cPr propargyl Ib893 OCF(CF₃)₂ Me—cPrpropargyl Ib894 OCF₂Cl Me—cPr propargyl Ib895 OCFCl₂ Me—cPr propargylIb896 OCCl₃ Me—cPr propargyl Ib897 CF₃ Me—cPr Me—CN Ib898 CHF₂ Me—cPrMe—CN Ib899 CF₂CF₃ Me—cPr Me—CN Ib900 CF(CF₃)₂ Me—cPr Me—CN Ib901COH(CF₃)₂ Me—cPr Me—CN Ib902 CF₂Cl Me—cPr Me—CN Ib903 CFCl₂ Me—cPr Me—CNIb904 CCl₃ Me—cPr Me—CN Ib905 OCF₃ Me—cPr Me—CN Ib906 OCHF₂ Me—cPr Me—CNIb907 OCF₂CF₃ Me—cPr Me—CN Ib908 OCF₂CHF₂ Me—cPr Me—CN Ib909 OCF(CF₃)₂Me—cPr Me—CN Ib910 OCF₂Cl Me—cPr Me—CN Ib911 OCFCl₂ Me—cPr Me—CN Ib912OCCl₃ Me—cPr Me—CN Ib913 CF₃ allyl allyl Ib914 CHF₂ allyl allyl Ib915CF₂CF₃ allyl allyl Ib916 CF(CF₃)₂ allyl allyl Ib917 COH(CF₃)₂ allylallyl Ib918 CF₂Cl allyl allyl Ib919 CFCl₂ allyl allyl Ib920 CCl₃ allylallyl Ib921 OCF₃ allyl allyl Ib922 OCHF₂ allyl allyl Ib923 OCF₂CF₃ allylallyl Ib924 OCF₂CHF₂ allyl allyl Ib925 OCF(CF₃)₂ allyl allyl Ib926OCF₂Cl allyl allyl Ib927 OCFCl₂ allyl allyl Ib928 OCCl₃ allyl allylIb929 CF₃ allyl propargyl Ib930 CHF₂ allyl propargyl Ib931 CF₂CF₃ allylpropargyl Ib932 CF(CF₃)₂ allyl propargyl Ib933 COH(CF₃)₂ allyl propargylIb934 CF₂Cl allyl propargyl Ib935 CFCl₂ allyl propargyl Ib936 CCl₃ allylpropargyl Ib937 OCF₃ allyl propargyl Ib938 OCHF₂ allyl propargyl Ib939OCF₂CF₃ allyl propargyl Ib940 OCF₂CHF₂ allyl propargyl Ib941 OCF(CF₃)₂allyl propargyl Ib942 OCF₂Cl allyl propargyl Ib943 OCFCl₂ allylpropargyl Ib944 OCCl₃ allyl propargyl Ib945 CF₃ allyl Me—CN Ib946 CHF₂allyl Me—CN Ib947 CF₂CF₃ allyl Me—CN Ib948 CF(CF₃)₂ allyl Me—CN Ib949COH(CF₃)₂ allyl Me—CN Ib950 CF₂Cl allyl Me—CN Ib951 CFCl₂ allyl Me—CNIb952 CCl₃ allyl Me—CN Ib953 OCF₃ allyl Me—CN Ib954 OCHF₂ allyl Me—CNIb955 OCF₂CF₃ allyl Me—CN Ib956 OCF₂CHF₂ allyl Me—CN Ib957 OCF(CF₃)₂allyl Me—CN Ib958 OCF₂Cl allyl Me—CN Ib959 OCFCl₂ allyl Me—CN Ib960OCCl₃ allyl Me—CN Ib961 CF₃ propargyl propargyl Ib962 CHF₂ propargylpropargyl Ib963 CF₂CF₃ propargyl propargyl Ib964 CF(CF₃)₂ propargylpropargyl Ib965 COH(CF₃)₂ propargyl propargyl Ib966 CF₂Cl propargylpropargyl Ib967 CFCl₂ propargyl propargyl Ib968 CCl₃ propargyl propargylIb969 OCF₃ propargyl propargyl Ib970 OCHF₂ propargyl propargyl Ib971OCF₂CF₃ propargyl propargyl Ib972 OCF₂CHF₂ propargyl propargyl Ib973OCF(CF₃)₂ propargyl propargyl Ib974 OCF₂Cl propargyl propargyl Ib975OCFCl₂ propargyl propargyl Ib976 OCCl₃ propargyl propargyl Ib977 CF₃propargyl Me—CN Ib978 CHF₂ propargyl Me—CN Ib979 CF₂CF₃ propargyl Me—CNIb980 CF(CF₃)₂ propargyl Me—CN Ib981 COH(CF₃)₂ propargyl Me—CN Ib982CF₂Cl propargyl Me—CN Ib983 CFCl₂ propargyl Me—CN Ib984 CCl₃ propargylMe—CN Ib985 OCF₃ propargyl Me—CN Ib986 OCHF₂ propargyl Me—CN Ib987OCF₂CF₃ propargyl Me—CN Ib988 OCF₂CHF₂ propargyl Me—CN Ib989 OCF(CF₃)₂propargyl Me—CN Ib990 OCF₂Cl propargyl Me—CN Ib991 OCFCl₂ propargylMe—CN Ib992 OCCl₃ propargyl Me—CN Ib993 CF₃ Me—CN Me—CN Ib994 CHF₂ Me—CNMe—CN Ib995 CF₂CF₃ Me—CN Me—CN Ib996 CF(CF₃)₂ Me—CN Me—CN Ib997COH(CF₃)₂ Me—CN Me—CN Ib998 CF₂Cl Me—CN Me—CN Ib999 CFCl₂ Me—CN Me—CNIb1000 CCl₃ Me—CN Me—CN Ib1001 OCF₃ Me—CN Me—CN Ib1002 OCHF₂ Me—CN Me—CNIb1003 OCF₂CF₃ Me—CN Me—CN Ib1004 OCF₂CHF₂ Me—CN Me—CN Ib1005 OCF(CF₃)₂Me—CN Me—CN Ib1006 OCF₂Cl Me—CN Me—CN Ib1007 OCFCl₂ Me—CN Me—CN Ib1008OCCl₃ Me—CN Me—CN Ib1009 CF₃ H Me Ib1010 CHF₂ H Me Ib1011 CF₂CF₃ H MeIb1012 CF(CF₃)₂ H Me Ib1013 COH(CF₃)₂ H Me Ib1014 CF₂Cl H Me Ib1015CFCl₂ H Me Ib1016 CCl₃ H Me Ib1017 OCF₃ H Me Ib1018 OCHF₂ H Me Ib1019OCF₂CF₃ H Me Ib1020 OCF₂CHF₂ H Me Ib1021 OCF(CF₃)₂ H Me Ib1022 OCF₂Cl HMe Ib1023 OCFCl₂ H Me Ib1024 OCCl₃ H Me Ib1025 CF₃ H Et Ib1026 CHF₂ H EtIb1027 CF₂CF₃ H Et Ib1028 CF(CF₃)₂ H Et Ib1029 COH(CF₃)₂ H Et Ib1030CF₂Cl H Et Ib1031 CFCl₂ H Et Ib1032 CCl₃ H Et Ib1033 OCF₃ H Et Ib1034OCHF₂ H Et Ib1035 OCF₂CF₃ H Et Ib1036 OCF₂CHF₂ H Et Ib1037 OCF(CF₃)₂ HEt Ib1038 OCF₂Cl H Et Ib1039 OCFCl₂ H Et Ib1040 OCCl₃ H Et Ib1041 CF₃ HPr Ib1042 CHF₂ H Pr Ib1043 CF₂CF₃ H Pr Ib1044 CF(CF₃)₂ H Pr Ib1045COH(CF₃)₂ H Pr Ib1046 CF₂Cl H Pr Ib1047 CFCl₂ H Pr Ib1048 CCl₃ H PrIb1049 OCF₃ H Pr Ib1050 OCHF₂ H Pr Ib1051 OCF₂CF₃ H Pr Ib1052 OCF₂CHF₂ HPr Ib1053 OCF(CF3)2 H Pr Ib1054 OCF₂Cl H Pr Ib1055 OCFCl₂ H Pr Ib1056OCCl₃ H Pr Ib1057 CF₃ H iPr Ib1058 CHF₂ H iPr Ib1059 CF₂CF₃ H iPr Ib1060CF(CF₃)₂ H iPr Ib1061 COH(CF₃)₂ H iPr Ib1062 CF₂Cl H iPr Ib1063 CFCl₂ HiPr Ib1064 CCl₃ H iPr Ib1065 OCF₃ H iPr Ib1066 OCHF₂ H iPr Ib1067OCF₂CF₃ H iPr Ib1068 OCF₂CHF₂ H iPr Ib1069 OCF(CF₃)₂ H iPr Ib1070 OCF₂ClH iPr Ib1071 OCFCl₂ H iPr Ib1072 OCCl₃ H iPr Ib1073 CF₃ H Bu Ib1074 CHF₂H Bu Ib1075 CF₂CF₃ H Bu Ib1076 CF(CF₃)₂ H Bu Ib1077 COH(CF₃)₂ H BuIb1078 CF₂Cl H Bu Ib1079 CFCl₂ H Bu Ib1080 CCl₃ H Bu Ib1081 OCF₃ H BuIb1082 OCHF₂ H Bu Ib1083 OCF₂CF₃ H Bu Ib1084 OCF₂CHF₂ H Bu Ib1085OCF(CF₃)₂ H Bu Ib1086 OCF₂Cl H Bu Ib1087 OCFCl₂ H Bu Ib1088 OCCl₃ H BuIb1089 CF₃ H Pn Ib1090 CHF₂ H Pn Ib1091 CF₂CF₃ H Pn Ib1092 CF(CF₃)₂ H PnIb1093 COH(CF₃)₂ H Pn Ib1094 CF₂Cl H Pn Ib1095 CFCl₂ H Pn Ib1096 CCl₃ HPn Ib1097 OCF₃ H Pn Ib1098 OCHF₂ H Pn Ib1099 OCF₂CF₃ H Pn Ib1100OCF₂CHF₂ H Pn Ib1101 OCF(CF₃)₂ H Pn Ib1102 OCF₂Cl H Pn Ib1103 OCFCl₂ HPn Ib1104 OCCl₃ H Pn Ib1105 CF₃ H Me—cPr Ib1106 CHF₂ H Me—cPr Ib1107CF₂CF₃ H Me—cPr Ib1108 CF(CF₃)₂ H Me—cPr Ib1109 COH(CF₃)₂ H Me—cPrIb1110 CF₂Cl H Me—cPr Ib1111 CFCl₂ H Me—cPr Ib1112 CCl₃ H Me—cPr Ib1113OCF₃ H Me—cPr Ib1114 OCHF₂ H Me—cPr Ib1115 OCF₂CF₃ H Me—cPr Ib1116OCF₂CHF₂ H Me—cPr Ib1117 OCF(CF3)2 H Me—cPr Ib1118 OCF₂Cl H Me—cPrIb1119 OCFCl₂ H Me—cPr Ib1120 OCCl₃ H Me—cPr Ib1121 CF₃ H allyl Ib1122CHF₂ H allyl Ib1123 CF₂CF₃ H allyl Ib1124 CF(CF₃)₂ H allyl Ib1125COH(CF₃)₂ H allyl Ib1126 CF₂Cl H allyl Ib1127 CFCl₂ H allyl Ib1128 CCl₃H allyl Ib1129 OCF₃ H allyl Ib1130 OCHF₂ H allyl Ib1131 OCF₂CF₃ H allylIb1132 OCF₂CHF₂ H allyl Ib1133 OCF(CF₃)₂ H allyl Ib1134 OCF₂Cl H allylIb1135 OCFCl₂ H allyl Ib1136 OCCl₃ H allyl Ib1137 CF₃ H propargyl Ib1138CHF₂ H propargyl Ib1139 CF₂CF₃ H propargyl Ib1140 CF(CF₃)₂ H propargylIb1141 COH(CF₃)₂ H propargyl Ib1142 CF₂Cl H propargyl Ib1143 CFCl₂ Hpropargyl Ib1144 CCl₃ H propargyl Ib1145 OCF₃ H propargyl Ib1146 OCHF₂ Hpropargyl Ib1147 OCF₂CF₃ H propargyl Ib1148 OCF₂CHF₂ H propargyl Ib1149OCF(CF₃)₂ H propargyl Ib1150 OCF₂Cl H propargyl Ib1151 OCFCl₂ Hpropargyl Ib1152 OCCl₃ H propargyl Ib1153 CF₃ H Me—CN Ib1154 CHF₂ HMe—CN Ib1155 CF₂CF₃ H Me—CN Ib1156 CF(CF₃)₂ H Me—CN Ib1157 COH(CF₃)₂ HMe—CN Ib1158 CF₂Cl H Me—CN Ib1159 CFCl₂ H Me—CN Ib1160 CCl₃ H Me—CNIb1161 OCF₃ H Me—CN Ib1162 OCHF₂ H Me—CN Ib1163 OCF₂CF₃ H Me—CN Ib1164OCF₂CHF₂ H Me—CN Ib1165 OCF(CF₃)₂ H Me—CN Ib1166 OCF₂Cl H Me—CN Ib1167OCFCl₂ H Me—CN Ib1168 OCCl₃ H Me—CN

Following annotation when used in the text are defined as follows:

Me is methyl or —CH₃;Et is ethyl or —CH₂CH₃;Pr is propyl or —(CH₂)₂CH₃,iPr is isopropyl or —CH(CH₃)₂;Bu is butyl or (CH₂)₃CH₃;Pn is pentyl or (CH₂)₄CH₃;Me-cPr is methylcyclopropyl;Me-CN is cyanomethyl.

Examples of compounds of this particular preferred embodiment of suchcompounds are the compounds I-a given in the following tables 1 to 13.

Table 1 Compounds of the formula I-a and their salts, wherein R^(5c) andR^(5d) are hydrogen, R^(5a) is H and the remaining variables R¹, R², R⁵band A correspond to each combination of the radicals numbered A1a1 toA1a197 with each row of Table C numbered Ib1 to Ib1168.

Table 2 Compounds of the formula I-a and their salts, wherein R^(5c) andR^(5d) are hydrogen, R^(5a) is F and the remaining variables R¹, R²,R^(5b) and A correspond to each combination of the radicals numberedA1a1 to A1a197 with each row of Table C numbered Ib1 to Ib1168.

Table 3 Compounds of the formula I-a and their salts, wherein R^(5d) andR^(5d) are hydrogen, R^(5a) is Cl and the remaining variables R¹, R²,R^(5b) and A correspond to each combination of the radicals numberedA1a1 to A1a197 with each row of Table C numbered Ib1 to Ib1168.

Table 4 Compounds of the formula I-a and their salts, wherein R^(5c) andR^(5d) are hydrogen, R^(5a) is Br and the remaining variables R¹, R²,R^(5b) and A correspond to each combination of the radicals numberedA1a1 to A1a197 with each row of Table C numbered Ib1 to Ib1168.

Table 5 Compounds of the formula I-a and their salts, wherein R^(5c) andR^(5d) are hydrogen, R^(5a) is I and the remaining variables R¹, R²,R^(5b) and A correspond to each combination of the radicals numberedA1a1 to A1a197 with each row of Table C numbered Ib1 to Ib1168.

Table 6 Compounds of the formula I-a and their salts, wherein R^(5c) andR^(5d) are hydrogen, R^(5a) is CN and the remaining variables R¹, R²,R^(5b) and A correspond to each combination of the radicals numberedA1a1 to A1a197 with each row of Table C numbered Ib1 to Ib1168.

Table 7 Compounds of the formula I-a and their salts, wherein R^(5c) andR^(5d) are hydrogen, R^(5a) is NO₂ and the remaining variables R¹, R²,R^(5b) and A correspond to each combination of the radicals numberedA1a1 to A1a197 with each row of Table C numbered Ib1 to Ib1168.

Table 8 Compounds of the formula I-a and their salts, wherein R^(5c) andR^(5d) are hydrogen, R^(5a) is CH₃ and the remaining variables R¹, R²,R^(5b) and A correspond to each combination of the radicals numberedA1a1 to A1a197 with each row of Table C numbered Ib1 to Ib1168.

Table 9 Compounds of the formula I-a and their salts, wherein R^(5c) andR^(5d) are hydrogen, R^(5a) is CF₃ and the remaining variables R¹, R²,R^(5b) and A correspond to each combination of the radicals numberedA1a1 to A1a197 with each row of Table C numbered Ib1 to Ib1168.

Table 10 Compounds of the formula I-a and their salts, wherein R^(5c)and R^(5d) are hydrogen, R^(5a) is CHF₂ and the remaining variables R¹,R², R^(5b) and A correspond to each combination of the radicals numberedA1a1 to A1a197 with each row of Table C numbered Ib1 to Ib1168.

Table 11 Compounds of the formula I-a and their salts, wherein R^(5c)and R^(5d) are hydrogen, R^(5a) is OCF₃ and the remaining variables R¹,R², R^(5b) and A correspond to each combination of the radicals numberedA1a1 to A1a197 with each row of Table C numbered Ib1 to Ib1168.

Table 12 Compounds of the formula I-a and their salts, wherein R^(5c)and R^(5d) are hydrogen, R^(5a) is OCHF₂ and the remaining variables R¹,R², R^(5b) and A correspond to each combination of the radicals numberedA1a1 to A1a197 with each row of Table C numbered Ib1 to Ib1168.

Table 13 Compounds of the formula I-a and their salts, wherein R^(5c)and R^(5d) are hydrogen, R^(5a) is SCF₃ and the remaining variables R¹,R², R^(5b) and A correspond to each combination of the radicals numberedA1a1 to A1a197 with each row of Table C numbered Ib1 to Ib1168.

Each example of the compounds of formula I-a as defined in the tables 1to 13 constitutes a preferred embodiment of the invention.

Especially preferred embodiment of the invention are the compounds I-awherein R^(5a), is hydrogen, A², A³, A⁴ are CH, and the remainingvariables R¹, R², R³, R⁴, R^(5b), A¹ are defined in each row of thefollowing Table D (variables R¹, R², R³, R⁴, R^(5b), A¹ are defined inradical A and Ib being respectively defined in table B and C):

TABLE D Radical A Ib A1a1 Ib1 A1a2 Ib1 A1a3 Ib1 A1a4 Ib1 A1a5 Ib1 A1a6Ib1 A1a7 Ib1 A1a8 Ib1 A1a9 Ib1 A1a10 Ib1 A1a11 Ib1 A1a12 Ib1 A1a13 Ib1A1a14 Ib1 A1a1 Ib17 A1a2 Ib17 A1a3 Ib17 A1a4 Ib17 A1a5 Ib17 A1a6 Ib17A1a7 Ib17 A1a8 Ib17 A1a9 Ib17 A1a10 Ib17 A1a11 Ib17 A1a12 Ib17 A1a13Ib17 A1a14 Ib17 A1a1 Ib33 A1a2 Ib33 A1a3 Ib33 A1a4 Ib33 A1a5 Ib33 A1a6Ib33 A1a7 Ib33 A1a8 Ib33 A1a9 Ib33 A1a10 Ib33 A1a11 Ib33 A1a12 Ib33A1a13 Ib33 A1a14 Ib33 A1a1 Ib49 A1a2 Ib49 A1a3 Ib49 A1a4 Ib49 A1a5 Ib49A1a6 Ib49 A1a7 Ib49 A1a8 Ib49 A1a9 Ib49 A1a10 Ib49 A1a11 Ib49 A1a12 Ib49A1a13 Ib49 A1a14 Ib49 A1a1 Ib65 A1a2 Ib65 A1a3 Ib65 A1a4 Ib65 A1a5 Ib65A1a6 Ib65 A1a7 Ib65 A1a8 Ib65 A1a9 Ib65 A1a10 Ib65 A1a11 Ib65 A1a12 Ib65A1a13 Ib65 A1a14 Ib65 A1a1 Ib81 A1a2 Ib81 A1a3 Ib81 A1a4 Ib81 A1a5 Ib81A1a6 Ib81 A1a7 Ib81 A1a8 Ib81 A1a9 Ib81 A1a10 Ib81 A1a11 Ib81 A1a12 Ib81A1a13 Ib81 A1a14 Ib81 A1a1 Ib97 A1a2 Ib97 A1a3 Ib97 A1a4 Ib97 A1a5 Ib97A1a6 Ib97 A1a7 Ib97 A1a8 Ib97 A1a9 Ib97 A1a10 Ib97 A1a11 Ib97 A1a12 Ib97A1a13 Ib97 A1a14 Ib97 A1a1 Ib113 A1a2 Ib113 A1a3 Ib113 A1a4 Ib113 A1a5Ib113 A1a6 Ib113 A1a7 Ib113 A1a8 Ib113 A1a9 Ib113 A1a10 Ib113 A1a11Ib113 A1a12 Ib113 A1a13 Ib113 A1a14 Ib113 A1a1 Ib129 A1a2 Ib129 A1a3Ib129 A1a4 Ib129 A1a5 Ib129 A1a6 Ib129 A1a7 Ib129 A1a8 Ib129 A1a9 Ib129A1a10 Ib129 A1a11 Ib129 A1a12 Ib129 A1a13 Ib129 A1a14 Ib129 A1a1 Ib145A1a2 Ib145 A1a3 Ib145 A1a4 Ib145 A1a5 Ib145 A1a6 Ib145 A1a7 Ib145 A1a8Ib145 A1a9 Ib145 A1a10 Ib145 A1a11 Ib145 A1a12 Ib145 A1a13 Ib145 A1a14Ib145 A1a1 Ib161 A1a2 Ib161 A1a3 Ib161 A1a4 Ib161 A1a5 Ib161 A1a6 Ib161A1a7 Ib161 A1a8 Ib161 A1a9 Ib161 A1a10 Ib161 A1a11 Ib161 A1a12 Ib161A1a13 Ib161 A1a14 Ib161 A1a1 Ib177 A1a2 Ib177 A1a3 Ib177 A1a4 Ib177 A1a5Ib177 A1a6 Ib177 A1a7 Ib177 A1a8 Ib177 A1a9 Ib177 A1a10 Ib177 A1a11Ib177 A1a12 Ib177 A1a13 Ib177 A1a14 Ib177 A1a1 Ib193 A1a2 Ib193 A1a3Ib193 A1a4 Ib193 A1a5 Ib193 A1a6 Ib193 A1a7 Ib193 A1a8 Ib193 A1a9 Ib193A1a10 Ib193 A1a11 Ib193 A1a12 Ib193 A1a13 Ib193 A1a14 Ib193 A1a1 Ib209A1a2 Ib209 A1a3 Ib209 A1a4 Ib209 A1a5 Ib209 A1a6 Ib209 A1a7 Ib209 A1a8Ib209 A1a9 Ib209 A1a10 Ib209 A1a11 Ib209 A1a12 Ib209 A1a13 Ib209 A1a14Ib209 A1a1 Ib225 A1a2 Ib225 A1a3 Ib225 A1a4 Ib225 A1a5 Ib225 A1a6 Ib225A1a7 Ib225 A1a8 Ib225 A1a9 Ib225 A1a10 Ib225 A1a11 Ib225 A1a12 Ib225A1a13 Ib225 A1a14 Ib225 A1a1 Ib241 A1a2 Ib241 A1a3 Ib241 A1a4 Ib241 A1a5Ib241 A1a6 Ib241 A1a7 Ib241 A1a8 Ib241 A1a9 Ib241 A1a10 Ib241 A1a11Ib241 A1a12 Ib241 A1a13 Ib241 A1a14 Ib241 A1a1 Ib257 A1a2 Ib257 A1a3Ib257 A1a4 Ib257 A1a5 Ib257 A1a6 Ib257 A1a7 Ib257 A1a8 Ib257 A1a9 Ib257A1a10 Ib257 A1a11 Ib257 A1a12 Ib257 A1a13 Ib257 A1a14 Ib257 A1a1 Ib273A1a2 Ib273 A1a3 Ib273 A1a4 Ib273 A1a5 Ib273 A1a6 Ib273 A1a7 Ib273 A1a8Ib273 A1a9 Ib273 A1a10 Ib273 A1a11 Ib273 A1a12 Ib273 A1a13 Ib273 A1a14Ib273 A1a1 Ib289 A1a2 Ib289 A1a3 Ib289 A1a4 Ib289 A1a5 Ib289 A1a6 Ib289A1a7 Ib289 A1a8 Ib289 A1a9 Ib289 A1a10 Ib289 A1a11 Ib289 A1a12 Ib289A1a13 Ib289 A1a14 Ib289 A1a1 Ib305 A1a2 Ib305 A1a3 Ib305 A1a4 Ib305 A1a5Ib305 A1a6 Ib305 A1a7 Ib305 A1a8 Ib305 A1a9 Ib305 A1a10 Ib305 A1a11Ib305 A1a12 Ib305 A1a13 Ib305 A1a14 Ib305 A1a1 Ib321 A1a2 Ib321 A1a3Ib321 A1a4 Ib321 A1a5 Ib321 A1a6 Ib321 A1a7 Ib321 A1a8 Ib321 A1a9 Ib321A1a10 Ib321 A1a11 Ib321 A1a12 Ib321 A1a13 Ib321 A1a14 Ib321 A1a1 Ib337A1a2 Ib337 A1a3 Ib337 A1a4 Ib337 A1a5 Ib337 A1a6 Ib337 A1a7 Ib337 A1a8Ib337 A1a9 Ib337 A1a10 Ib337 A1a11 Ib337 A1a12 Ib337 A1a13 Ib337 A1a14Ib337 A1a1 Ib353 A1a2 Ib353 A1a3 Ib353 A1a4 Ib353 A1a5 Ib353 A1a6 Ib353A1a7 Ib353 A1a8 Ib353 A1a9 Ib353 A1a10 Ib353 A1a11 Ib353 A1a12 Ib353A1a13 Ib353 A1a14 Ib353 A1a1 Ib369 A1a2 Ib369 A1a3 Ib369 A1a4 Ib369 A1a5Ib369 A1a6 Ib369 A1a7 Ib369 A1a8 Ib369 A1a9 Ib369 A1a10 Ib369 A1a11Ib369 A1a12 Ib369 A1a13 Ib369 A1a14 Ib369 A1a1 Ib385 A1a2 Ib385 A1a3Ib385 A1a4 Ib385 A1a5 Ib385 A1a6 Ib385 A1a7 Ib385 A1a8 Ib385 A1a9 Ib385A1a10 Ib385 A1a11 Ib385 A1a12 Ib385 A1a13 Ib385 A1a14 Ib385 A1a1 Ib401A1a2 Ib401 A1a3 Ib401 A1a4 Ib401 A1a5 Ib401 A1a6 Ib401 A1a7 Ib401 A1a8Ib401 A1a9 Ib401 A1a10 Ib401 A1a11 Ib401 A1a12 Ib401 A1a13 Ib401 A1a14Ib401 A1a1 Ib417 A1a2 Ib417 A1a3 Ib417 A1a4 Ib417 A1a5 Ib417 A1a6 Ib417A1a7 Ib417 A1a8 Ib417 A1a9 Ib417 A1a10 Ib417 A1a11 Ib417 A1a12 Ib417A1a13 Ib417 A1a14 Ib417 A1a1 Ib433 A1a2 Ib433 A1a3 Ib433 A1a4 Ib433 A1a5Ib433 A1a6 Ib433 A1a7 Ib433 A1a8 Ib433 A1a9 Ib433 A1a10 Ib433 A1a11Ib433 A1a12 Ib433 A1a13 Ib433 A1a14 Ib433 A1a1 Ib449 A1a2 Ib449 A1a3Ib449 A1a4 Ib449 A1a5 Ib449 A1a6 Ib449 A1a7 Ib449 A1a8 Ib449 A1a9 Ib449A1a10 Ib449 A1a11 Ib449 A1a12 Ib449 A1a13 Ib449 A1a14 Ib449 A1a1 Ib465A1a2 Ib465 A1a3 Ib465 A1a4 Ib465 A1a5 Ib465 A1a6 Ib465 A1a7 Ib465 A1a8Ib465 A1a9 Ib465 A1a10 Ib465 A1a11 Ib465 A1a12 Ib465 A1a13 Ib465 A1a14Ib465 A1a1 Ib481 A1a2 Ib481 A1a3 Ib481 A1a4 Ib481 A1a5 Ib481 A1a6 Ib481A1a7 Ib481 A1a8 Ib481 A1a9 Ib481 A1a10 Ib481 A1a11 Ib481 A1a12 Ib481A1a13 Ib481 A1a14 Ib481 A1a1 Ib497 A1a2 Ib497 A1a3 Ib497 A1a4 Ib497 A1a5Ib497 A1a6 Ib497 A1a7 Ib497 A1a8 Ib497 A1a9 Ib497 A1a10 Ib497 A1a11Ib497 A1a12 Ib497 A1a13 Ib497 A1a14 Ib497 A1a1 Ib513 A1a2 Ib513 A1a3Ib513 A1a4 Ib513 A1a5 Ib513 A1a6 Ib513 A1a7 Ib513 A1a8 Ib513 A1a9 Ib513A1a10 Ib513 A1a11 Ib513 A1a12 Ib513 A1a13 Ib513 A1a14 Ib513 A1a1 Ib529A1a2 Ib529 A1a3 Ib529 A1a4 Ib529 A1a5 Ib529 A1a6 Ib529 A1a7 Ib529 A1a8Ib529 A1a9 Ib529 A1a10 Ib529 A1a11 Ib529 A1a12 Ib529 A1a13 Ib529 A1a14Ib529 A1a1 Ib545 A1a2 Ib545 A1a3 Ib545 A1a4 Ib545 A1a5 Ib545 A1a6 Ib545A1a7 Ib545 A1a8 Ib545 A1a9 Ib545 A1a10 Ib545 A1a11 Ib545 A1a12 Ib545A1a13 Ib545 A1a14 Ib545 A1a1 Ib561 A1a2 Ib561 A1a3 Ib561 A1a4 Ib561 A1a5Ib561 A1a6 Ib561 A1a7 Ib561 A1a8 Ib561 A1a9 Ib561 A1a10 Ib561 A1a11Ib561 A1a12 Ib561 A1a13 Ib561 A1a14 Ib561 A1a1 Ib577 A1a2 Ib577 A1a3Ib577 A1a4 Ib577 A1a5 Ib577 A1a6 Ib577 A1a7 Ib577 A1a8 Ib577 A1a9 Ib577A1a10 Ib577 A1a11 Ib577 A1a12 Ib577 A1a13 Ib577 A1a14 Ib577 A1a1 Ib593A1a2 Ib593 A1a3 Ib593 A1a4 Ib593 A1a5 Ib593 A1a6 Ib593 A1a7 Ib593 A1a8Ib593 A1a9 Ib593 A1a10 Ib593 A1a11 Ib593 A1a12 Ib593 A1a13 Ib593 A1a14Ib593 A1a1 Ib609 A1a2 Ib609 A1a3 Ib609 A1a4 Ib609 A1a5 Ib609 A1a6 Ib609A1a7 Ib609 A1a8 Ib609 A1a9 Ib609 A1a10 Ib609 A1a11 Ib609 A1a12 Ib609A1a13 Ib609 A1a14 Ib609 A1a1 Ib625 A1a2 Ib625 A1a3 Ib625 A1a4 Ib625 A1a5Ib625 A1a6 Ib625 A1a7 Ib625 A1a8 Ib625 A1a9 Ib625 A1a10 Ib625 A1a11Ib625 A1a12 Ib625 A1a13 Ib625 A1a14 Ib625 A1a1 Ib641 A1a2 Ib641 A1a3Ib641 A1a4 Ib641 A1a5 Ib641 A1a6 Ib641 A1a7 Ib641 A1a8 Ib641 A1a9 Ib641A1a10 Ib641 A1a11 Ib641 A1a12 Ib641 A1a13 Ib641 A1a14 Ib641 A1a1 Ib657A1a2 Ib657 A1a3 Ib657 A1a4 Ib657 A1a5 Ib657 A1a6 Ib657 A1a7 Ib657 A1a8Ib657 A1a9 Ib657 A1a10 Ib657 A1a11 Ib657 A1a12 Ib657 A1a13 Ib657 A1a14Ib657 A1a1 Ib673 A1a2 Ib673 A1a3 Ib673 A1a4 Ib673 A1a5 Ib673 A1a6 Ib673A1a7 Ib673 A1a8 Ib673 A1a9 Ib673 A1a10 Ib673 A1a11 Ib673 A1a12 Ib673A1a13 Ib673 A1a14 Ib673 A1a1 Ib689 A1a2 Ib689 A1a3 Ib689 A1a4 Ib689 A1a5Ib689 A1a6 Ib689 A1a7 Ib689 A1a8 Ib689 A1a9 Ib689 A1a10 Ib689 A1a11Ib689 A1a12 Ib689 A1a13 Ib689 A1a14 Ib689 A1a1 Ib705 A1a2 Ib705 A1a3Ib705 A1a4 Ib705 A1a5 Ib705 A1a6 Ib705 A1a7 Ib705 A1a8 Ib705 A1a9 Ib705A1a10 Ib705 A1a11 Ib705 A1a12 Ib705 A1a13 Ib705 A1a14 Ib705 A1a1 Ib721A1a2 Ib721 A1a3 Ib721 A1a4 Ib721 A1a5 Ib721 A1a6 Ib721 A1a7 Ib721 A1a8Ib721 A1a9 Ib721 A1a10 Ib721 A1a11 Ib721 A1a12 Ib721 A1a13 Ib721 A1a14Ib721 A1a1 Ib737 A1a2 Ib737 A1a3 Ib737 A1a4 Ib737 A1a5 Ib737 A1a6 Ib737A1a7 Ib737 A1a8 Ib737 A1a9 Ib737 A1a10 Ib737 A1a11 Ib737 A1a12 Ib737A1a13 Ib737 A1a14 Ib737 A1a1 Ib753 A1a2 Ib753 A1a3 Ib753 A1a4 Ib753 A1a5Ib753 A1a6 Ib753 A1a7 Ib753 A1a8 Ib753 A1a9 Ib753 A1a10 Ib753 A1a11Ib753 A1a12 Ib753 A1a13 Ib753 A1a14 Ib753 A1a1 Ib769 A1a2 Ib417 A1a3Ib769 A1a4 Ib769 A1a5 Ib769 A1a6 Ib769 A1a7 Ib769 A1a8 Ib769 A1a9 Ib769A1a10 Ib769 A1a11 Ib769 A1a12 Ib769 A1a13 Ib769 A1a14 Ib769 A1a1 Ib785A1a2 Ib785 A1a3 Ib785 A1a4 Ib785 A1a5 Ib785 A1a6 Ib785 A1a7 Ib785 A1a8Ib785 A1a9 Ib785 A1a10 Ib785 A1a11 Ib785 A1a12 Ib785 A1a13 Ib785 A1a14Ib785 A1a1 Ib801 A1a2 Ib801 A1a3 Ib801 A1a4 Ib801 A1a5 Ib801 A1a6 Ib801A1a7 Ib801 A1a8 Ib801 A1a9 Ib801 A1a10 Ib801 A1a11 Ib801 A1a12 Ib801A1a13 Ib801 A1a14 Ib801 A1a1 Ib817 A1a2 Ib817 A1a3 Ib817 A1a4 Ib817 A1a5Ib817 A1a6 Ib817 A1a7 Ib817 A1a8 Ib817 A1a9 Ib817 A1a10 Ib817 A1a11Ib817 A1a12 Ib817 A1a13 Ib817 A1a14 Ib817 A1a1 Ib833 A1a2 Ib833 A1a3Ib833 A1a4 Ib833 A1a5 Ib833 A1a6 Ib833 A1a7 Ib833 A1a8 Ib833 A1a9 Ib833A1a10 Ib833 A1a11 Ib833 A1a12 Ib833 A1a13 Ib833 A1a14 Ib833 A1a1 Ib849A1a2 Ib849 A1a3 Ib849 A1a4 Ib849 A1a5 Ib849 A1a6 Ib849 A1a7 Ib849 A1a8Ib849 A1a9 Ib849 A1a10 Ib849 A1a11 Ib849 A1a12 Ib849 A1a13 Ib849 A1a14Ib849 A1a1 Ib865 A1a2 Ib865 A1a3 Ib865 A1a4 Ib865 A1a5 Ib865 A1a6 Ib865A1a7 Ib865 A1a8 Ib865 A1a9 Ib865 A1a10 Ib865 A1a11 Ib865 A1a12 Ib865A1a13 Ib865 A1a14 Ib865 A1a1 Ib881 A1a2 Ib881 A1a3 Ib881 A1a4 Ib881 A1a5Ib881 A1a6 Ib881 A1a7 Ib881 A1a8 Ib881 A1a9 Ib881 A1a10 Ib881 A1a11Ib881 A1a12 Ib881 A1a13 Ib881 A1a14 Ib881 A1a1 Ib897 A1a2 Ib897 A1a3Ib897 A1a4 Ib897 A1a5 Ib897 A1a6 Ib897 A1a7 Ib897 A1a8 Ib897 A1a9 Ib897A1a10 Ib897 A1a11 Ib897 A1a12 Ib897 A1a13 Ib897 A1a14 Ib897 A1a1 Ib913A1a2 Ib913 A1a3 Ib913 A1a4 Ib913 A1a5 Ib913 A1a6 Ib913 A1a7 Ib913 A1a8Ib913 A1a9 Ib913 A1a10 Ib913 A1a11 Ib913 A1a12 Ib913 A1a13 Ib913 A1a14Ib913 A1a1 Ib929 A1a2 Ib929 A1a3 Ib929 A1a4 Ib929 A1a5 Ib929 A1a6 Ib929A1a7 Ib929 A1a8 Ib929 A1a9 Ib929 A1a10 Ib929 A1a11 Ib929 A1a12 Ib929A1a13 Ib929 A1a14 Ib929 A1a1 Ib945 A1a2 Ib945 A1a3 Ib945 A1a4 Ib945 A1a5Ib945 A1a6 Ib945 A1a7 Ib945 A1a8 Ib945 A1a9 Ib945 A1a10 Ib945 A1a11Ib945 A1a12 Ib945 A1a13 Ib945 A1a14 Ib945 A1a1 Ib961 A1a2 Ib961 A1a3Ib961 A1a4 Ib961 A1a5 Ib961 A1a6 Ib961 A1a7 Ib961 A1a8 Ib961 A1a9 Ib961A1a10 Ib961 A1a11 Ib961 A1a12 Ib961 A1a13 Ib961 A1a14 Ib961 A1a1 Ib977A1a2 Ib977 A1a3 Ib977 A1a4 Ib977 A1a5 Ib977 A1a6 Ib977 A1a7 Ib977 A1a8Ib977 A1a9 Ib977 A1a10 Ib977 A1a11 Ib977 A1a12 Ib977 A1a13 Ib977 A1a14Ib977 A1a1 Ib993 A1a2 Ib993 A1a3 Ib993 A1a4 Ib993 A1a5 Ib993 A1a6 Ib993A1a7 Ib993 A1a8 Ib993 A1a9 Ib993 A1a10 Ib993 A1a11 Ib993 A1a12 Ib993A1a13 Ib993 A1a14 Ib993 A1a1 Ib1009 A1a2 Ib1009 A1a3 Ib1009 A1a4 Ib1009A1a5 Ib1009 A1a6 Ib1009 A1a7 Ib1009 A1a8 Ib1009 A1a9 Ib1009 A1a10 Ib1009A1a11 Ib1009 A1a12 Ib1009 A1a13 Ib1009 A1a14 Ib1009 A1a1 Ib1025 A1a2Ib1025 A1a3 Ib1025 A1a4 Ib1025 A1a5 Ib1025 A1a6 Ib1025 A1a7 Ib1025 A1a8Ib1025 A1a9 Ib1025 A1a10 Ib1025 A1a11 Ib1025 A1a12 Ib1025 A1a13 Ib1025A1a14 Ib1025 A1a1 Ib1041 A1a2 Ib1041 A1a3 Ib1041 A1a4 Ib1041 A1a5 Ib1041A1a6 Ib1041 A1a7 Ib1041 A1a8 Ib1041 A1a9 Ib1041 A1a10 Ib1041 A1a11Ib1041 A1a12 Ib1041 A1a13 Ib1041 A1a14 Ib1041 A1a1 Ib1057 A1a2 Ib1057A1a3 Ib1057 A1a4 Ib1057 A1a5 Ib1057 A1a6 Ib1057 A1a7 Ib1057 A1a8 Ib1057A1a9 Ib1057 A1a10 Ib1057 A1a11 Ib1057 A1a12 Ib1057 A1a13 Ib1057 A1a14Ib1057 A1a1 Ib1073 A1a2 Ib1073 A1a3 Ib1073 A1a4 Ib1073 A1a5 Ib1073 A1a6Ib1073 A1a7 Ib1073 A1a8 Ib1073 A1a9 Ib1073 A1a10 Ib1073 A1a11 Ib1073A1a12 Ib1073 A1a13 Ib1073 A1a14 Ib1073 A1a1 Ib1089 A1a2 Ib1089 A1a3Ib1089 A1a4 Ib1089 A1a5 Ib1089 A1a6 Ib1089 A1a7 Ib1089 A1a8 Ib1089 A1a9Ib1089 A1a10 Ib1089 A1a11 Ib1089 A1a12 Ib1089 A1a13 Ib1089 A1a14 Ib1089A1a1 Ib1105 A1a2 Ib1105 A1a3 Ib1105 A1a4 Ib1105 A1a5 Ib1105 A1a6 Ib1105A1a7 Ib1105 A1a8 Ib1105 A1a9 Ib1105 A1a10 Ib1105 A1a11 Ib1105 A1a12Ib1105 A1a13 Ib1105 A1a14 Ib1105 A1a1 Ib1121 A1a2 Ib1121 A1a3 Ib1121A1a4 Ib1121 A1a5 Ib1121 A1a6 Ib1121 A1a7 Ib1121 A1a8 Ib1121 A1a9 Ib1121A1a10 Ib1121 A1a11 Ib1121 A1a12 Ib1121 A1a13 Ib1121 A1a14 Ib1121 A1a1Ib1137 A1a2 Ib1137 A1a3 Ib1137 A1a4 Ib1137 A1a5 Ib1137 A1a6 Ib1137 A1a7Ib1137 A1a8 Ib1137 A1a9 Ib1137 A1a10 Ib1137 A1a11 Ib1137 A1a12 Ib1137A1a13 Ib1137 A1a14 Ib1137 A1a1 Ib1153 A1a2 Ib1153 A1a3 Ib1153 A1a4Ib1153 A1a5 Ib1153 A1a6 Ib1153 A1a7 Ib1153 A1a8 Ib1153 A1a9 Ib1153 A1a10Ib1153 A1a11 Ib1153 A1a12 Ib1153 A1a13 Ib1153 A1a14 Ib1153

Compounds of formula I can be prepared according to the followingmethods and variations described in schemes 1-5. The variables R¹, R²,R³, R⁴, R^(5a), R^(5b), R^(5c), R^(5d), A¹, A², A³, A⁴, and p aredefined as above for formula I.

Compounds of formula I can, for example, be prepared by reaction ofamines (or salts thereof) and quinazolines of the formula 4 as describedby, for example, Ananthan et al, Bioorg. Med. Chem. Lett. 2002, 12, 2225and outlined in Scheme 1. Depending on the conditions, bases such astriethylamine or potassium carbonate may be necessary. The reaction canbe run in a wide variety of solvents including Tetrahydrofuran (THF),dioxane, and isopropanol or the like. The corresponding quinazolines ofthe formula 4 containing a leaving group (LG) wherein LG is a fluorine,chlorine, bromine, iodine, thioethers, sulfonates or another suitableleaving group can be prepared from quinazolinones of the formula 3 forexample by reaction with a halogenating agent such as phosphorusoxychloride, phosphorus trichloride, phosphorus pentachloride, thionylchloride, phosphorus tribromide, phosphorus triiodide as described, forexample, by Hayakawa, Bioorg. Med. Chem. 2006, 14, 6847. Depending onthe conditions solvents such as dioxane, ether, toluene, DMF or the likecan be employed. Quinazolinones of the formula 3 can be prepared fromanthranilamides of formula 1 and aldehydes of formula 2 in the presenceof reagents such as iron chloride (or hydrates thereof), iodine, sodiumbisulfite or 2,3-dichloro-4,5-dicyano-1,4-benzoquinone as described, forexample, by Wang et al, Bull. Chem. Soc. Jpn. 2006, 79, 1426.

Quinazolinones of the formula 3 can also be prepared as outlined inScheme 2 from arylhalides of the formula 7 and amidines of the formula 8under copper catalysis as described, for example, by Liu, Angew. Chem.Int. Ed. 2009, 48, 348. Alternatively, quinazolinones of the formula 3can be prepared from anilines 5 and nitriles 6 under acidic conditions(e.g. hydrochloric acid) as described, for example, by Bogolubsky et al,J. Comb. Chem. 2008, 10, 858 for from amides of the formula 9 underbasic conditions (e.g. sodium hydroxide) as described, for example, byRoy et al, J. Org. Chem. 2006, 71, 382.

Aminoquinazolines of the formula (I) can be prepared as outlined inScheme 3 by a coupling reaction between intermediates of the formula 13and intermediates of the formula 14 in the presence of metal catalystderived from, for example, palladium, platinum, iron, copper or nickelwhere LG or Y are, for example, a fluorine, chlorine, bromine, iodine,triflate, thioether, boronic acid, boronate ester, trifluoroborate, organoborane or organostannane or other suitable leaving group, Aphosphine-, amine-, sulfoxide-derived ligand and base such as potassiumcarbonate or triethylemine may also be required for the reaction asdescribed, for example, by Itoh et al, Adv. Syn. Cat. 2004, 346, 1859.Intermediate of the formula 13 can be prepared from dichloroquinazolineof the formula 12 where LG is an analogous leaving group as describedabove. In turn the corresponding quinazolines of the formula 12 can beprepared from quinazoline-2,4-diones of the formula 11 using a similarmethod to that used to prepare intermediates of the formula 4.Quinazoline-2,4-diones of the formula 11 can be prepared fromanthranilic acids of the formula 10 using reagents such as urea,isocyanate, thioisocyanate as described, for example, by Smits et al, J.Med. Chem. 2008, 7855.

Anthranilamides of the formula 1 can be prepared following an analogousroute as that described in Scheme 4 [T. Sandmeyer, Helv. Chinn. Acta1919, 2, 234 or S. J. Garden et al, Tetrahedron Lett. 1997, 38(9), 1501]starting from isatoic anhydrides of the formula 18 in one step using areagent such as ammonia or in two steps using an amine-based nucleophilesuch an benzylamine, hydroxylamine or azide followed by reduction with,for example, hydrogen or ammonium formate as described, for example byKlaubert et al, J. Med. Chem. 1981, 24, 742 and Singh et at J.Heterocyclic Chem. 1990, 27, 2101. Isatoic anhydrides of the formula 18can be synthesized from indole-2,3-diones of the formula 17 by oxidationwith e.g. meta-chloroperbenzoic acid [G. M. Coppola, J. HeterocyclicChem. 1987, 24, 1249], hydrogen peroxide or chromic acid in a solventsuch as dichloromethane, acetic acid or water. In turn indole-2,3-dionesof the formula 17 can be prepared in a Friedel-Crafts-type reaction fromisonitrosoacetanilides of the formula 16 using a protic or Lewis acidsuch as sulfuric acid or aluminium trichloride. Finallyisonitrosoacetanilides of the formula 16 can be prepared fromsubstituted anilines of the formula 15 using chloral and hydroxylamineas reagents.

Anthranilamides of the formula 1, bearing strongly electron withdrawingsubstituents on the phenyl ring, are accessible through correspondingindole-2,3-diones of the formula 17 which in turn can be preparedfollowing a route as that described by P. Hewawasam et al, TetrahedronLett. 1994, 35, 7303 and which is outlined in Scheme 5.Indole-2,3-diones of the formula 17 can be prepared by treatment ofoxoacetic acid esters of the formula 20 with acids such as hydrochloricacid, trifluoroacetic acid, and triflic acid in solvents such as THF,water or CH₂Cl₂ as described, for example, by Hamashima et al., J. Am.Chem. Soc. 2005, 127, 10154. In turn oxoacetic acid esters of theformula 20, R^(x) being for example ethyl, methyl, can be prepared byexposure of carbamates of the formula 19 to strong carbon bases such asn-, sec-, or t-BuLi followed by reaction of the resultant carbanion withoxoacetic acid diesters. Finally carbamates of the formula 19 can beprepared from anilines of the formula 15 by reaction withdi-t-butyldicarbonate.

If individual compounds cannot be prepared via the above-describedroutes, they can be prepared by derivatization of other compounds I orby customary modifications of the synthesis routes described.

The reaction mixtures are worked up in the customary manner, for exampleby mixing with water, separating the phases, and, if appropriate,purifying the crude products by chromatography, for example on aluminaor silica gel. Some of the intermediates and end products may beobtained in the form of colorless or pale brown viscous oils, which arefreed or purified from volatile components under reduced pressure and atmoderately elevated temperature. If the intermediates and end productsare obtained as solids, they may be purified by recrystallization ordigestion.

The present invention also provides a method for controllinginvertebrate pests which method comprises treating the pests, their foodsupply, their habitat or their breeding ground or a cultivated plant,plant propagation materials (such as seed), soil, area, material orenvironment in which the pests are growing or may grow, or thematerials, cultivated plants, plant propagation materials (such asseed), soils, surfaces or spaces to be protected from pest attack orinfestation with a pesticidally effective amount of a compound offormula I or a salt or N-oxide thereof or a composition as definedabove.

Preferably, the method of the invention serves for protecting plantpropagation material (such as seed) and the plant which grows therefromfrom invertebrate pest attack or infestation and comprises treating theplant propagation material (such as seed) with a pesticidally effectiveamount of a compound of formula I or an agriculturally acceptable saltor N-oxide thereof as defined above or with a pesticidally effectiveamount of an agricultural composition as defined above and below. Themethod of the invention is not limited to the protection of the“substrate” (plant, plant propagation materials, soil material etc.)which has been treated according to the invention, but also has apreventive effect, thus, for example, according protection to a plantwhich grows from a treated plant propagation materials (such as seed),the plant itself not having been treated.

In the sense of the present invention, “invertebrate pests” arepreferably selected from arthropods and nematodes, more preferably fromharmful insects, arachnids and nematodes, and even more preferably frominsects, acarids and nematodes. In the sense of the present invention,“invertebrate pests” are most preferably insects.

The invention further provides an agricultural composition for combatingsuch invertebrate pests, which comprises such an amount of at least onecompound of the general formula I or at least one agriculturally usefulsalt or N-oxide thereof and at least one inert liquid and/or solidagronomically acceptable carrier that has a pesticidal action and, ifdesired, at least one surfactant.

Such a composition may contain a single active compound of the formula Ior a salt or N-oxide thereof or a mixture of several active compounds Ior their salts according to the present invention. The compositionaccording to the present invention may comprise an individual isomer ormixtures of isomers as well as individual tautomers or mixtures oftautomers.

The compounds of the formula I and the pestidicidal compositionscomprising them are effective agents for controlling arthropod pests andnematodes. Invertebrate pests controlled by the compounds of formula Iinclude for example

insects from the order of the lepidopterans (Lepidoptera), for exampleAgrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsiagemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius,Cacoecia murinana, Capua reticulana, Chematobia brumata, Choristoneurafumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydiapomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella,Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella,Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholithafunebrana, Grapholitha molesta, Heliothis armigera, Heliothis virescens,Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea,Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina fiscellaria,Laphygma exigua, Leucoptera coffeella, Leucoptera scitella,Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis,Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosomaneustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis,Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalerabucephala, Phthorimaea operculella, Phyllocnistis citrella, Pierisbrassicae, Plathypena scabra, Plutella xylostella, Pseudoplusiaincludens, Rhyacionia frustrana, Scrobipalpula absoluta, Sitotrogacerealella, Sparganothis pilleriana, Spodoptera frugiperda, Spodopteralittoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrixviridana, Trichoplusiani and Zeiraphera canadensis;

beetles (Coleoptera), for example Agrilus sinuatus, Agriotes lineatus,Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar,Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Blastophaguspiniperda, Blitophaga undata, Bruchus rufi-manus, Bruchus pisorum,Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cero-tomatrifurcata, Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnematibi-alis, Conoderus vespertinus, Crioceris asparagi, Diabroticalongicornis, Diabrotica 12 punctata, Diabrotica virgifera, Epilachnavarivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobiusabietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lemabilineata, Lema melanopus, Leptinotarsa decemlineata, Limoniuscalifornicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethesaeneus, Melolontha hip-pocastani, Melolontha melolontha, Oulema oryzae,Ortiorrhynchus sulcatus, Otiorrhyn-chus ovatus, Phaedon cochleariae,Phyllotreta chrysocephala, Phyllophaga sp., Phyl-lopertha horticola,Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitonalineatus and Sitophilus granaria;

dipterans (Diptera), for example Aedes aegypti, Aedes vexans, Anastrephaludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana,Chrysomya homi-nivorax, Chrysomya macellaria, Contarinia sorghicola,Cordylobia anthropophaga, Culex pipiens, Dacus cucurbitae, Dacus oleae,Dasineura brassicae, Fannia canicularis, Gasterophilus intestinalis,Glossina morsitans, Haematobia irritans, Haplodiplosis equestris,Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyzatrifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoriapectoralis, Mayetiola destruc-tor, Musca domestica, Muscina stabulans,Oestrus ovis, Oscinella frit, Pegomya hyso-cyami, Phorbia antiqua,Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletispomonella, Tabanus bovinus, Tipula oleracea and Tipula paludosa;

thrips (Thysanoptera), e.g. Dichromothrips corbetti, Frankliniellafusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothripscitri, Thrips oryzae, Thrips palmi and Thrips tabaci;

hymenopterans (Hymenoptera), e.g. Athalia rosae, Atta cephalotes, Attasexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea,Monomorium pharaonis, So-lenopsis geminata and Solenopsis invicta;

heteropterans (Heteroptera), e.g. Acrosternum hilare, Blissusleucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercusintermedius, Eurygaster integriceps, Euschistus impictiventris,Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezaraviridula, Piesma quadrata, Solubea insularis and Thyanta perditor;

homopterans (Homoptera), e.g. Acyrthosiphon onobrychis, Adelges laricis,Aphidula nasturtii, Aphis fabae, Aphis forbesi, Aphis pomi, Aphisgossypii, Aphis grossulariae, Aphis schneideri, Aphis spiraecola, Aphissambuci, Acyrthosiphon pisum, Aulacorthum solani, Bemisia argentifolii,Bemisia tabaci, Brachycaudus cardui, Brachycaudus helichrysi,Brachycaudus persicae, Brachycaudus prunicola, Brevicoryne brassicae,Capitophorus horni, Cerosipha gossypii, Chaetosiphon fragaefolii,Cryptomyzus ribis, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphisradicola, Dysaulacorthum pseudosolani, Dysaphis plantaginea, Dysaphispyri, Empoasca fabae, Hyalopterus pruni, Hyperomyzus lactucae,Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megouraviciae, Melanaphis pyrarius, Metopolophium dirhodum, Myzodes persicae,Myzus ascalonicus, Myzus cerasi, Myzus persicae, Myzus varians,Nasonovia ribis-nigri, Nilaparvata lugens, Pemphigus bursarius,Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla pini,Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Rhopalosiphum padi,Rhopalosiphum insertum, Sappaphis mala, Sappaphis mali, Schizaphisgraminum, Schizoneura lanuginosa, Sitobion avenae, Sogatella furciferaTrialeurodes vaporariorum, Toxoptera aurantiiand, and Viteus vitifolii;

termites (Isoptera), e.g. Calotermes flavicollis, Leucotermes flavipes,Reticulitermes flavipes, Reticulitermes lucifugus and Termes natalensis;

orthopterans (Orthoptera), e.g. Acheta domestica, Blatta orientalis,Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa,Locusta migratoria, Melanoplus bivittatus, Melanoplus femur-rubrum,Melanoplus mexicanus, Melanoplus sanguinipes, Melano-plus spretus,Nomadacris septemfasciata, Periplaneta americana, Schistocercaameri-cana, Schistocerca peregrina, Stauronotus maroccanus andTachycines asynamorus;

arachnoidea, such as arachnids (Acarina), e.g. of the familiesArgasidae, Ixodidae and Sarcoptidae, such as Amblyomma americanum,Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilusdecoloratus, Boophilus microplus, Dermacentor silvarum, Hyalommatruncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus moubata,Otobius megnini, Dermanyssus gallinae, Psoroptes ovis, Rhipicephalusappendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, andEriophyidae spp. such as Aculus schlechtendali, Phyllocoptrata oleivoraand Eriophyes sheldoni; Tarsonemidae spp. such as Phytonemus pallidusand Polyphagotarsonemus latus; Tenuipalpidae spp. such as Brevipalpusphoenicis; Tetranychidae spp. such as Tetranychus cinnabarinus,Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius andTetranychus urticae, Panonychus ulmi, Panonychus citri, and oligonychuspratensis;

siphonatera, e.g. Xenopsylla cheopsis, Ceratophyllus spp.

The compositions and compounds of formula I are useful for the controlof nematodes, especially plant parasitic nematodes such as root knotnematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogynejavanica, and other Meloidogyne species;

cyst-forming nematodes, Globodera rostochiensis and other Globoderaspecies; Het-erodera avenae, Heterodera glycines, Heterodera schachtii,Heterodera trifolii, and other Heterodera species; Seed gall nematodes,Anguina species; Stem and foliar nematodes, Aphelenchoides species;Sting nematodes, Belonolaimus longicaudatus and other Belonolaimusspecies; Pine nematodes, Bursaphelenchus xylophilus and otherBursaphelenchus species; Ring nematodes, Criconema species, Criconemellaspecies, Criconemoides species, Mesocriconema species; Stem and bulbnematodes, Ditylenchus destructor, Ditylenchus dipsaci and otherDitylenchus species; Awl nema-todes, Dolichodorus species; Spiralnematodes, Heliocotylenchus multicinctus and other Helicotylenchusspecies; Sheath and sheathoid nematodes, Hemicycliophora species andHemicriconemoides species; Hirshmanniella species; Lance nematodes,Hoploaimus species; false rootknot nematodes, Nacobbus species; Needlenematodes, Longidorus elongatus and other Longidorus species; Pinnematodes, Paratylen-chus species; Lesion nematodes, Pratylenchusneglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchusgoodeyi and other Pratylenchus species; Burrowing nematodes, Radopholussimilis and other Radopholus species; Reniform nematodes, Rotylenchusrobustus and other Rotylenchus species; Scutellonema species; Stubbyroot nematodes, Trichodorus primitivus and other Trichodorus species,Paratrichodorus species; Stunt nematodes, Tylenchorhynchus claytoni,Tylenchorhynchus dubius and other Tylenchorhynchus species; Citrusnematodes, Tylenchulus species; Dagger nematodes, Xiphinema species; andother plant parasitic nematode species.

In a preferred embodiment of the invention the compounds of formula Iare used for controlling insects or arachnids, in particular insects ofthe orders Lepidoptera, Coleoptera, Thysanoptera and Homoptera andarachnids of the order Acarina. The compounds of the formula I accordingto the present invention are particularly useful for controlling insectsof the order Thysanoptera and Homoptera.

The compounds of formula I or the pesticidal compositions comprisingthem may be used to protect growing plants and crops from attack orinfestation by invertebrate pests, especially insects, acaridae orarachnids by contacting the plant/crop with a pesticidally effectiveamount of compounds of formula I. The term “crop” refers both to growingand harvested crops.

The compounds of formula I can be converted into the customaryformulations, for example solutions, emulsions, suspensions, dusts,powders, pastes and granules. The use form depends on the particularintended purpose; in each case, it should ensure a fine and evendistribution of the compound according to the invention.

The formulations are prepared in a known manner (see e.g. for reviewU.S. Pat. No. 3,060,084, EP-A 707 445 (for liquid concentrates),Browning, “Agglomeration”, Chemical Engi-neering, Dec. 4, 1967, 147-48,Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York,1963, pages 8-57 and of seq. WO 91/13546, U.S. Pat. No. 4,172,714, U.S.Pat. No. 4,144,050, U.S. Pat. No. 3,920,442, U.S. Pat. No. 5,180,587,U.S. Pat. No. 5,232,701, U.S. Pat. No. 5,208,030, GB 2,095,558, U.S.Pat. No. 3,299,566, Klingman, Weed Control as a Science, John Wiley andSons, Inc., New York, 1961, Hance et al., Weed Control Handbook, 8thEd., Blackwell Scientific Publications, Oxford, 1989 and Mollet, H.,Grubermann, A., Formulation tech-nology, Wiley VCH Verlag GmbH, Weinheim(Germany), 2001, 2. D. A. Knowles, Chemistry and Technology ofAgrochemical Formulations, Kluwer Academic Publishers, Dordrecht, 1998(ISBN 0-7514-0443-8), for example by extending the active compound withauxiliaries suitable for the formulation of agrochemicals, such assolvents and/or carriers, if desired emulsifiers, surfactants anddispersants, preservatives, anti-foaming agents, anti-freezing agents,for seed treatment formulation also optionally colorants and/or bindersand/or gelling agents.

Examples of suitable solvents are water, aromatic solvents (for exampleSolvesso products, xylene), paraffins (for example mineral oilfractions), alcohols (for example methanol, butanol, pentanol, benzylalcohol), ketones (for example cyclohexanone, gamma-butyrolactone),pyrrolidones (N-methylpyrrolidone [NMP], N-octylpyrrolidone [NOP]),acetates (glycol diacetate), glycols, fatty acid dimethylamides, fattyacids and fatty acid esters. In principle, solvent mixtures may also beused.

Suitable emulsifiers are non-ionic and anionic emulsifiers (for examplepolyoxyethylene fatty alcohol ethers, alkylsulfonates andarylsulfonates).

Examples of dispersants are lignin-sulfite waste liquors andmethylcellulose.

Suitable surfactants used are alkali metal, alkaline earth metal andammonium salts of lignosulfonic acid, naphthalenesulfonic acid,phenolsulfonic acid, dibutylnaphthalene-sulfonic acid,alkylarylsulfonates, alkyl sulphates, alkylsulfonates, fatty alcoholsulfates, fatty acids and sulphated fatty alcohol glycol ethers,furthermore condensates of sulfonated naphthalene and naphthalenederivatives with formaldehyde, condensates of naphthalene or ofnaphthalenesulfonic acid with phenol and formaldehyde, polyoxyethyleneoctylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol,alkylphenol polyglycol ethers, tributylphenyl polyglycol ether,tristearylphenyl polyglycol ether, alkylaryl polyether alcohols, alcoholand fatty alcohol ethylene, oxide condensates, ethoxylated castor oil,polyoxyethylene alkyl ethers, ethoxylated polyoxypropyl-ene, laurylalcohol polyglycol ether acetal, sorbitol esters, lignosulfite wasteliquors and methylcellulose.

Substances which are suitable for the preparation of directly sprayablesolutions, emulsions, pastes or oil dispersions are mineral oilfractions of medium to high boiling point, such as kerosene or dieseloil, furthermore coal tar oils and oils of vegetable or animal origin,aliphatic, cyclic and aromatic hydrocarbons, for example toluene,xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or theirderivatives, methanol, etha-nol, propanol, butanol, cyclohexanol,cyclohexanone, isophorone, highly polar solvents, for example dimethylsulfoxide, N-methylpyrrolidone or water.

Also anti-freezing agents such as glycerin, ethylene glycol, propyleneglycol and bactericides such as can be added to the formulation.

Suitable antiforming agents are for example antiforming agents based onsilicon or magnesium stearate.

A suitable preservative is e.g. dichlorophen.

Seed treatment formulations may additionally comprise binders andoptionally color-ants.

Binders can be added to improve the adhesion of the active materials onthe seeds after treatment. Suitable binders are block copolymers EO/POsurfactants but also polyvinylalcoholsl, polyvinylpyrrolidones,polyacrylates, polymethacrylates, polybute-nes, polyisobutylenes,polystyrene, polyethyleneamines, polyethyleneamides, poly-ethyleneimines(Lupasol®, Polymin®), polyethers, polyurethans, polyvinylacetate,ty-lose and copolymers derived from these polymers.

Optionally, also colorants can be included in the formulation. Suitablecolorants or dyes for seed treatment formulations are Rhodamin B, C.I.Pigment Red 112, C.I. Solvent Red 1, pigment blue 15:4, pigment blue15:3, pigment blue 15:2, pigment blue 15:1, pigment blue 80, pigmentyellow 1, pigment yellow 13, pigment red 112, pigment red 48:2, pigmentred 48:1, pigment red 57:1, pigment red 53:1, pigment orange 43, pigmentorange 34, pigment orange 5, pigment green 36, pigment green 7, pigmentwhite 6, pigment brown 25, basic violet 10, basic violet 49, acid red51, acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10,basic red 108.

An example of a gelling agent is carrageen (Satiagel®).

Powders, materials for spreading and dustable products can be preparedby mixing or concomitantly grinding the active substances with a solidcarrier.

Granules, for example coated granules, impregnated granules andhomogeneous granules, can be prepared by binding the active compounds tosolid carriers.

Examples of solid carriers are mineral earths such as silica gels,silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess,clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate,magnesium oxide, ground synthetic materials, fertilizers, such as, forexample, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas,and products of vegetable origin, such as cereal meal, tree bark meal,wood meal and nutshell meal, cellulose powders and other solid carriers.

In general, the formulations comprise from 0.01 to 95% by weight,preferably from 0.1 to 90% by weight, of the active compound(s). In thiscase, the active compound(s) are employed in a purity of from 90% to 100by weight, preferably 95% to 100% % by weight (according to NMRspectrum).

For seed treatment purposes, respective formulations can be diluted 2-to 10-fold leading to concentrations in the ready to use preparations of0.01 to 60% by weight active compound by weight, preferably 0.1 to 40%by weight.

The compounds of formula I can be used as such, in the form of theirformulations or the use forms prepared therefrom, for example in theform of directly sprayable solutions, powders, suspensions ordispersions, emulsions, oil dispersions, pastes, dustable products,materials for spreading, or granules, by means of spraying, atomizing,dusting, spreading or pouring. The use forms depend entirely on theintended purposes; they are intended to ensure in each case the finestpossible distribution of the active compound(s) according to theinvention.

Aqueous use forms can be prepared from emulsion concentrates, pastes orwetable powders (sprayable powders, oil dispersions) by adding water. Toprepare emulsions, pastes or oil dispersions, the substances, as such ordissolved in an oil or solvent, can be homogenized in water by means ofa wetting agent, tackifier, dispersant or emulsifier. However, it isalso possible to prepare concentrates composed of active substance,wetting agent, tackifier, dispersant or emulsifier and, if appropriate,solvent or oil, and such concentrates are suitable for dilution withwater.

The active compound concentrations in the ready-to-use preparations canbe varied within relatively wide ranges. In general, they are from0.0001 to %10, preferably from 0.01 to 1% per weight.

The active compound(s) may also be used successfully in theultra-low-volume process (ULV), it being possible to apply formulationscomprising over 95% by weight of active compound, or even to apply theactive compound without additives.

The following are examples of formulations:

1. Products for dilution with water for foliar applications. For seedtreatment purposes, such products may be applied to the seed diluted orundiluted.A) Water-soluble concentrates (SL, LS)10 parts by weight of the active compound(s) are dissolved in 90 partsby weight of water or a water-soluble solvent, As an alternative,wetting agents or other auxiliaries are added. The active compound(s)dissolves upon dilution with water, whereby a formula-tion with 10%(w/w) of active compound(s) is obtained.B) Dispersible concentrates (DC)20 parts by weight of the active compound(s) are dissolved in 70 partsby weight of cyclohexanone with addition of 10 parts by weight of adispersant, for example polyvi-nylpyrrolidone. Dilution with water givesa dispersion, whereby a formulation with 20% (w/w) of active compound(s)is obtained.Emulsifiable concentrates (EC)15 parts by weight of the active compound(s) are dissolved in 7 parts byweight of xy-lene with addition of calcium dodecylbenzenesulfonate andcastor oil ethoxylate (in each case 5 parts by weight). Dilution withwater gives an emulsion, whereby a formulation with 15% (w/w) of activecompound(s) is obtained.

Emulsions (EW, EO, ES)

25 parts by weight of the active compound(s) are dissolved in 35 partsby weight of xylene with addition of calcium dodecylbenzenesulfonate andcastor oil ethoxylate (in each case 5 parts by weight). This mixture isintroduced into 30 parts by weight of wa-ter by means of an emulsifiermachine (e.g. Ultraturrax) and made into a homogeneous emulsion.Dilution with water gives an emulsion, whereby a formulation with 25%(w/w) of active compound(s) is obtained.

E) Suspensions (SC, OD, FS)

In an agitated ball mill, 20 parts by weight of the active compound(s)are comminuted with addition of 10 parts by weight of dispersants,wetting agents and 70 parts by weight of water or of an organic solventto give a fine active compound(s) suspension. Dilution with water givesa stable suspension of the active compound(s), whereby a formulationwith 20% (w/w) of active compound(s) is obtained.F) Water-dispersible granules and water-soluble granules (WG, SG)50 parts by weight of the active compound(s) are ground finely withaddition of 50 parts by weight of dispersants and wetting agents andmade as water-dispersible or water-soluble granules by means oftechnical appliances (for example extrusion, spray tower, fluidizedbed). Dilution with water gives a stable dispersion or solution of theactive compound(s), whereby a formulation with 50% (w/w) of activecompound(s) is obtained.Water-dispersible powders and water-soluble powders (WP, SP, SS, WS)75 parts by weight of the active compound(s) are ground in arotor-stator mill with addition of 25 parts by weight of dispersants,wetting agents and silica gel. Dilution with water gives a stabledispersion or solution of the active compound(s), whereby a formulationwith 75% (w/w) of active compound(s) is obtained.

H) Gel-Formulation (GF)

In an agitated ball mill, 20 parts by weight of the active compound(s)are comminuted with addition of 10 parts by weight of dispersants, 1part by weight of a gelling agent wetting agents and 70 parts by weightof water or of an organic solvent to give a fine active compound(s)suspension. Dilution with water gives a stable suspension of the activecompound(s), whereby a formulation with 20% (w/w) of active compound(s)is obtained.2. Products to be applied undiluted for foliar applications. For seedtreatment purposes, such products may be applied to the seed diluted orundiluted.I) Dustable powders (DP, DS)5 parts by weight of the active compound(s) are ground finely and mixedintimately with 95 parts by weight of finely divided kaolin. This givesa dustable product having 5% (w/w) of active compound(s)

J) Granules (GR, FG, GG, MG)

0.5 parts by weight of the active compound(s) is ground finely andassociated with 95.5 parts by weight of carriers, whereby a formulationwith 0.5% (w/w) of active corn-pound(s) is obtained. Current methods areextrusion, spray-drying or the fluidized bed. This gives granules to beapplied undiluted for foliar use.K) ULV solutions (UL)10 parts by weight of the active compound(s) are dissolved in 90 partsby weight of an organic solvent, for example xylene. This gives aproduct having 10% (w/w) of active compound(s), which is appliedundiluted for foliar use.

The compounds of formula I are also suitable for the treatment of plantpropagation materials (such as seed). Conventional seed treatmentformulations include for example flowable concentrates FS, solutions LS,powders for dry treatment DS, water dispersible'powders for slurrytreatment WS, water-soluble powders SS and emulsion ES and EC and gelformulation GF. These formulations can be applied to the seed diluted orundiluted. Application to the seeds is carried out before sowing, eitherdirectly on the seeds or after having pre-germinated the latter

In a preferred embodiment a FS formulation is used for seed treatment.Typically, a FS formulation may comprise 1 to 800 g/l of activeingredient, 1 to 200 g/l surfactant, 0 to 200 g/l antifreezing agent, 0to 400 g/l of binder, 0 to 200 g/l of a pigment and up to 1 liter of asolvent, preferably water.

Other preferred FS formulations of compounds of formula I for seedtreatment comprise from 0.5 to 80 wt of the active ingredient, from 0.05to 5 wt of a wetting agent, from 0.5 to 15 wt of a dispersing agent,from 0.1 to 5 wt of a thickener, from 5 to 20 wt of an anti-freezeagent, from 0.1 to 2 wt of an anti-foam agent, from 1 to 20 wt of apigment and/or a dye, from 0 to 15 wt of a sticker/adhesion agent, from0 to 75 wt of a filler/vehicle, and from 0.01 to 1 wt of a preservative.

Various types of oils, wetting agents, adjuvants, herbicides,fungicides, other pesticides, or bactericides may be added to the activeingredients, if appropriate just immediately prior to use (tank mix).These agents usually are admixed with the agents according to theinvention in a weight ratio of 1:10 to 10:1.

The compounds of formula I are effective through both contact (via soil,glass, wall, bed net, carpet, plant parts or animal parts), andingestion (bait, or plant part).

For use against ants, termites, wasps, flies, mosquitoes, crickets, orcockroaches, com-pounds of formula I are preferably used in a baitcomposition.

The bait can be a liquid, a solid or a semisolid preparation (e.g. agel). Solid baits can be formed into various shapes and forms suitableto the respective application e.g. granules, blocks, sticks, disks.Liquid baits can be filled into various devices to ensure properapplication, e.g. open containers, spraying devices, droplet sources, orevaporation sources. Gels can be based on aqueous or oily matrices andcan be formulated to particular necessities in terms of stickiness,moisture retention or aging characteristics.

The bait employed in the composition is a product, which is sufficientlyattractive to incite insects such as ants, termites, wasps, flies,mosquitoes, crickets etc. or cockroaches to eat it. The attractivenesscan be manipulated by using feeding stimulants or sex pheromones. Foodstimulants are chosen, for example, but not exclusively, from animaland/or plant proteins (meat-, fish- or blood meal, insect parts, eggyolk), from fats and oils of animal and/or plant origin, or mono-,oligo- or polyorganosaccharides, especially from sucrose, lactose,fructose, dextrose, glucose, starch, pectin or even molasses or honey.Fresh or decaying parts of fruits, crops, plants, animals, insects orspecific parts thereof can also serve as a feeding stimulant. Sexpheromones are known to be more insect specific. Specific pheromones aredescribed in the literature and are known to those skilled in the art.

Formulations of compounds of formula I as aerosols (e.g. in spray cans),oil sprays or pump sprays are highly suitable for the non-professionaluser for controlling pests such as flies, fleas, ticks, mosquitos orcockroaches. Aerosol recipes are preferably corn-posed of the activecompound, solvents such as lower alcohols (e.g. methanol, ethanol,propanol, butanol), ketones (e.g. acetone, methyl ethyl ketone),paraffin hydrocar-bons (e.g. kerosenes) having boiling ranges ofapproximately 50 to 250° C., dimethyl-formamide, N-methylpyrrolidone,dimethyl sulphoxide, aromatic hydrocarbons such as toluene, xylene,water, furthermore auxiliaries such as emulsifiers such as sorbitolmonooleate, oleyl ethoxylate having 3 to 7 mol of ethylene oxide, fattyalcohol ethoxylate, perfume oils such as ethereal oils, esters of mediumfatty acids with lower alcohols, aromatic carbonyl compounds, ifappropriate stabilizers such as sodium benzoate, am-photericsurfactants, lower epoxides, triethyl orthoformate and, if required,propellants such as propane, butane, nitrogen, compressed air, dimethylether, carbon dioxide, nitrous oxide, or mixtures of these gases.

The oil spray formulations differ from the aerosol recipes in that nopropellants are used.

The compounds of formula I and their respective compositions can also beused in mosquito and fumigating coils, smoke cartridges, vaporizerplates or long-term vaporizers and also in moth papers, moth pads orother heat-independent vaporizer systems.

Methods to control infectious diseases transmitted by insects (e.g.malaria, dengue and yellow fever, lymphatic filariasis, andleishmaniasis) with compounds of formula I and its respectivecompositions also comprise treating surfaces of huts and houses, airspraying and impregnation of curtains, tents, clothing items, bed nets,tsetse-fly trap or the like. Insecticidal compositions for applicationto fibers, fabric, knitgoods, non-wovens, netting material or foils andtarpaulins preferably comprise a mixture including the insecticide,optionally a repellent and at least one binder. Suitable repellents forexample are N,N-diethyl-meta-toluamide (DEET),N,N-diethylphenylacetamide (DEPA),1-(3-cyclohexan-1-yl-carbonyl)-2-methylpiperine,(2-hydroxymethylcyclohexyl)acetic acid lactone, 2-ethyl-1,3-hexandiol,indalone, Methylneodecanamide (MNDA), a pyrethroid not used for insectcontrol such as{(+/−)-3-allyl-2-methyl-4-oxocyclopent-2-(+)-enyl-(+)-trans-chrysantemate(Esbiothrin), a repellent derived from or identical with plant extractslike limonene, eugenol, (+)-Eucamalol (1), (−)-1-epi-eucamalol or crudeplant extracts from plants like Eucalyptus maculata, Vitex rotundifolia,Cymbopogan martinii, Cymbopogan citratus (lemon grass), Cymopogannartdus (citronella). Suitable binders are selected for example frompolymers and copolymers of vinyl esters of aliphatic acids (such as suchas vinyl acetate and vinyl versatate), acrylic and methacrylic esters ofalcohols, such as butyl acrylate, 2-ethylhexylacrylate, and methylacrylate, mono- and diethylenically unsaturated hydrocarbons, such asstyrene, and aliphatic diens, such as butadiene.

The impregnation of curtains and bednets is done in general by dippingthe textile ma-terial into emulsions or dispersions of the activecompounds of formula I or spraying them onto the nets.

Methods which can be employed for treating the seed are, in principle,all suitable seed treatment and especially seed dressing techniquesknown in the art, such as seed coating (e.g. seed pelleting), seeddusting and seed imbibition (e.g. seed soaking). Here, “seed treatment”refers to all methods that bring seeds and the compounds of formula Iinto contact with each other, and “seed dressing” to methods of seedtreatment which provide the seeds with an amount of the compounds offormula I, i.e. which generate a seed comprising the compound of formulaI. In principle, the treatment can be applied to the seed at any timefrom the harvest of the seed to the sowing of the seed. The seed can betreated immediately before, or during, the planting of the seed, forexample using the “planter's box” method. However, the treatment mayalso be carried out several weeks or months, for example up to 12months, before planting the seed, for example in the form of a seeddressing treatment, without a substantially reduced efficacy beingobserved.

Expediently, the treatment is applied to unsown seed. As used herein,the term “unsown seed” is meant to include seed at any period from theharvest of the seed to the sowing of the seed in the ground for thepurpose of germination and growth of the plant.

Specifically, a procedure is followed in the treatment in which the seedis mixed, in a suitable device, for example a mixing device for solid orsolid/liquid mixing partners, with the desired amount of seed treatmentformulations, either as such or after previ-ous dilution with water,until the composition is distributed uniformly on the seed. Ifap-propriate, this is followed by a drying step.

The compounds of formula I, or the enantiomers, diastereomers orveterinarily acceptable salts thereof are in particular also suitablefor being used for combating parasites in and on animals.

An object of the present invention is therefore also to provide newmethods to control parasites in and on animals. Another object of theinvention is to provide safer pesticides for animals. Another object ofthe invention is further to provide pesticides for animals that may beused in lower doses than existing pesticides. And another object of theinvention is to provide pesticides for animals, which provide a longresidual control of the parasites.

The invention also relates to compositions containing a parasiticidallyeffective amount of compounds of formula I or the enantiomers orveterinarily acceptable salts thereof and an acceptable carrier, forcombating parasites in and on animals.

The present invention also provides a method for treating, controlling,preventing and protecting animals against infestation and infection byparasites, which comprises orally, topically or parenterallyadministering or applying to the animals a parasiticidally effectiveamount of a compound of formula I or the enantiomers or veterinarilyacceptable salts thereof or a composition comprising it.

The present invention also provides a non-therapeutic method fortreating, controlling, preventing and protecting animals againstinfestation and infection by parasites, which comprises applying to alocus a parasiticidally effective amount of a compound of formula I orthe enantiomers or veterinarily acceptable salts thereof or acomposition comprising it. The invention also provides a process for thepreparation of a composition for treating, controlling, preventing orprotecting animals against infestation or infection by parasites whichcomprises including a parasiticidally effective amount of a compound offormula I or the enantiomers or veterinarily acceptable salts thereof ina composition comprising it.

The invention relates further to the use of compounds of formula I fortreating, controlling, preventing or protecting animals againstinfestation or infection by parasites.

The invention relates also to the use of a compound of formula I, or acomposition comprising it, for the manufacture of a medicament for thetherapeutic treatment of animals against infections or infestions byparasites.

Activity of compounds against agricultural pests does not suggest theirsuitability for control of endo- and ectoparasites in and on animalswhich requires, for example, low, non-emetic dosages in the case of oralapplication, metabolic compatibility with the animal, low toxicity, anda safe handling.

Surprisingly it has now been found that compounds of formula I aresuitable for combating endo- and ectoparasites in and on animals. Thecompounds of formula I or the enantiomers or veterinarily acceptablesalts thereof and compositions comprising them are suitable for systemicand/or non-systemic control of ecto- and/or endoparasites. They areactive against all or some stages of development.

Compounds of formula I or the enantiomers or veterinarily acceptablesalts thereof and compositions comprising them are preferably used forcontrolling and preventing infestations and infections animals includingwarm-blooded animals (including humans) and fish. They are for examplesuitable for controlling and preventing infestations and infections inmammals such as cattle, sheep, swine, camels, deer, horses, pigs,poultry, rabbits, goats, dogs and cats, water buffalo, donkeys, fallowdeer and reindeer, and also in fur-bearing animals such as mink,chinchilla and raccoon, birds such as hens, geese, turkeys and ducks andfish such as fresh- and salt-water fish such as trout, carp and eels.

Compounds of formula I or the enantiomers or veterinarily acceptablesalts thereof and compositions comprising them are preferably used forcontrolling and preventing infestations and infections in domesticanimals, such as dogs or cats.

Infestations in warm-blooded animals and fish include, but are notlimited to lice, biting lice, ticks, nasal bots, keds, biting flies,muscoid flies, flies, myiasitic fly larvae, chiggers, gnats, mosquitoesand fleas.

The compounds of formula I are especially useful for combatingectoparasites.

The compounds of formula I are especially useful for combatingendoparasites.

The compounds of formula I are especially useful for combating parasitesof the following orders and species, respectively:

fleas (Siphonaptera), e.g. Ctenocephalides felis, Ctenocephalides canis,Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllusfasciatus,

cockroaches (Blattaria-Blattodea), e.g. Blattella germanica, Blattellaasahinae, Periplaneta americana, Periplaneta japonica, Periplanetabrunnea, Periplaneta fuligginosa, Periplaneta australasiae, and Blattaorientalis,

flies, mosquitoes (Diptera), e.g. Aedes aegypti, Aedes albopictus, Aedesvexans, Anastrepha ludens, Anopheles maculipennis, Anopheles crucians,Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anophelesleucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphoravicina, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria,Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyiahominivorax, Cordylobia anthropophaga, Culicoides furens, Culex pipiens,Culex nigripalpus, Culex quinque fasciatus, Culex tarsalis, Culisetainornata, Culiseta melanura, Dermatobia hominis, Fannia canicularis,Gasterophilus intestinalis, Glossina morsitans, Glossina palpalis,Glossina fuscipes, Glossina tachinoides, Haematobia irritans,Haplodiplosis equestris, Hippelates spp., Hypoderma lineata, Leptoconopstorrens, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoriapectoralis, Mansonia spp., Musca domestica, Muscina stabulans, Oestrusovis, Phlebotomus argentipes, Psorophora columbiae, Psorophora discolor,Prosimulium mixtum, Sarcophaga haemorrhoidalis, Sarcophaga sp., Simuliumvittatum, Stomoxys calcitrans, Tabanus bovinus, Tabanus atratus, Tabanuslineola, and Tabanus similis,

lice (Phthiraptera), e.g. Pediculus humanus capitis, Pediculus humanuscorporis, Pthirus pubis, Haematopinus eurysternus, Haematopinus suis,Linognathus vituli, Bovicola bovis, Menopon gallinae, Menacanthusstramineus and Solenopotes capillatus.

ticks and parasitic mites (Parasitiformes): ticks (Ixodida), e.g. Ixodesscapularis, Ixodes holocyclus, Ixodes pacificus, Rhiphicephalussanguineus, Dermacentor andersonii Dermacentor variabilis, Amblyommaamericanum, Ambryomma maculatum, Ornithodorus hermsi, Ornithodorusturicata and parasitic mites (Mesostigmata), e.g. Ornithonyssus bacotiand Dermanyssus gallinae,

Actinedida (Prostigmata) and Acaridida (Astigmata) e.g. Acarapis spp.,Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp.,Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp.,Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp.,Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp.,Notoedres spp., Knemidocoptes spp., Cytodites spp., and Laminosioptesspp,

Bugs (Heteropterida); Cimex lectularius, Cimex hemipterus, Reduviussenilis, Triatoma spp., Rhodnius ssp., Panstrongylus ssp. and Ariluscritatus,

Anoplurida, e.g. Haematopinus spp., Linognathus spp., Pediculus spp.,Phtirus spp., and Solenopotes spp,

Mallophagida (suborders Arnblycerina and Ischnocerina), e.g. Trimenoponspp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp.,Lepikentron spp., Trichodectes spp., and Felicola spp,

Roundworms Nematoda:

Wipeworms and Trichinosis (Trichosyringida), e.g. Trichinellidae(Trichinella spp.), (Trichuridae) Trichuris spp., Capillaria spp,

Rhabditida, e.g. Rhabditis spp, Strongyloides spp., Helicephalobus spp,

Strongylida, e.g. Strongylus spp., Ancylostoma spp., Necator americanus,Bunostomum spp. (Hookworm), Trichostrongylus spp., Haemonchuscontortus., Ostertagia spp., Cooperia spp., Nematodirus spp.,Dictyocaulus spp., Cyathostoma spp., Oesophagostomum spp., Stephanurusdentatus, Ollulanus spp., Chabertia spp., Stephanurus dentatus, Syngamustrachea, Ancylostoma spp., Uncinaria spp., Globocephalus spp., Necatorspp., Metastrongylus spp., Muellerius capillaris, Protostrongylus spp.,Angiostrongylus spp., Parelaphostrongylus spp. Aleurostrongylusabstrusus, and Dioctophyma renale,

Intestinal roundworms (Ascaridida), e.g. Ascaris lumbricoides, Ascarissuum, Ascaridia galli, Parascaris equorum, Enterobius vermicularis(Threadworm), Toxocara canis, Toxascaris leonine, Skrjabinema spp., andOxyuris equi,

Camallanida, e.g. Dracunculus medinensis (guinea worm)

Spirurida, e.g. Thelazia spp. Wuchereria spp., Brugia spp., Onchocercaspp., Dirofilari spp.a, Dipetalonema spp., Setaria spp., Elaeophoraspp., Spirocerca lupi, and Habronema spp.,

Thorny headed worms (Acanthocephala), e.g. Acanthocephalus spp.,Macracanthorhynchus hirudinaceus and Oncicola spp,

Planarians (Plathelminthes):

Flukes (Trematoda), e.g. Faciola spp., Fascioloides magna, Paragonimusspp., Dicrocoelium spp., Fasciolopsis buski, Clonorchis sinensis,Schistosoma spp., Trichobilharzia spp., Alaria alata, Paragonimus spp.,and Nanocyetes spp,

Cercomeromorpha, in particular Cestoda (Tapeworms), e.g.Diphyllobothrium spp., Tenia spp., Echinococcus spp., Dipylidiumcaninum, Multiceps spp., Hymenolepis spp., Mesocestoides spp.,Vampirolepis spp., Moniezia spp., Anoplocephala spp., Sirometra spp.,Anoplocephala spp., and Hymenolepis spp.

Applications

The present invention relates to the therapeutic and the non-therapeuticuse of compounds of formula I for controlling and/or combating parasitesin and/or on animals.

The compounds of formula I may be used to protect the animals fromattack or infestation by parasites by contacting them with aparasitically effective amount of compounds of formula I. As such,“contacting” includes both direct contact (applying thecompounds/compositions directly on the parasite, including theapplication directly on the animal or excluding the application directlyon the animal, e.g. at it's locus for the latter) and indirect contact(applying the compounds/compositions to the locus of the parasite). Thecontact of the parasite through application to its locus is an exampleof a non-therapeutic use of compounds of formula I.

“Locus” as defined above means the habitat, food supply, breedingground, area, material or environment in which a parasite is growing ormay grow outside of the animal. The compounds of the invention can alsobe applied preventively to places at which occurrence of the pests orparasites is expected.

The compounds of formula I can be effective through both contact (viasoil, glass, wall, bed net, carpet, blankets or animal parts) andingestion (e.g. baits).

The administration can be carried out prophylactically, therapeuticallyor non-therapeutically.

Administration of the active compounds is carried out directly or in theform of suitable preparations, orally, topically/dermally orparenterally.

In general, “parasiticidally effective amount” means the amount ofactive ingredient needed to achieve an observable effect on growth,including the effects of necrosis, death, retardation, prevention, andremoval, destruction, or otherwise diminishing the occurrence andactivity of the target organism. The parasiticidally effective amountcan vary for the various compounds/compositions used in the invention. Aparasiticidally effective amount of the compositions will also varyaccording to the prevailing conditions such as desired parasiticidaleffect and duration, target species, mode of application, and the like.

Generally it is favorable to apply the compounds of formula I in totalamounts of 0.5 mg/kg to 100 mg/kg per day, preferably 1 mg/kg to 50mg/kg per day.

Formulations

For oral administration to warm-blooded animals, the formula I compoundsmay be formulated as animal feeds, animal feed premixes, animal feedconcentrates, pills, solutions, pastes, suspensions, drenches, gels,tablets, boluses and capsules. In addition, the formula I compounds maybe administered to the animals in their drinking, water. For oraladministration, the dosage form chosen should provide the animal with0.01 mg/kg to 100 mg/kg of animal body weight per day of the formula Icompound, preferably with 0.5 mg/kg to 100 mg/kg of animal body weightper day.

Alternatively, the formula I compounds may be administered to animalsparenterally, for example, by intraruminal, intramuscular, intravenousor subcutaneous injection. The formula I compounds may be dispersed ordissolved in a physiologically acceptable carrier for subcutaneousinjection. Alternatively, the formula I compounds may be formulated intoan implant for subcutaneous administration. In addition the formula Icompound may be transdermally administered to animals. For parenteraladministration, the dosage form chosen should provide the animal with0.01 mg/kg to 100 mg/kg of animal body weight per day of the formula Icompound.

The formula I compounds may also be applied topically to the animals inthe form of dips, dusts, powders, collars, medallions, sprays, shampoos,spot-on and pour-on formulations and in ointments or oil-in-water orwater-in-oil emulsions. For topical application, dips and sprays usuallycontain 0.5 ppm to 5,000 ppm and preferably 1 ppm to 3,000 ppm of theformula I compound. In addition, the formula I compounds may beformulated as ear tags for animals, particularly quadrupeds such ascattle and sheep.

Suitable preparations are:

-   -   Solutions such as oral solutions, concentrates for oral        administration after dilution, solutions for use on the skin or        in body cavities, pouring-on formulations, gels;    -   Emulsions and suspensions for oral or dermal administration;        semi-solid preparations;    -   Formulations in which the active compound is processed in an        ointment base or in an oil-in-water or water-in-oil emulsion        base;    -   Solid preparations such as powders, premixes or concentrates,        granules, pellets, tablets, boluses, capsules; aerosols and        inhalants, and active compound-containing shaped articles.

Compositions suitable for injection are prepared by dissolving theactive ingredient in a suitable solvent and optionally adding furtheringredients such as acids, bases, buffer salts, preservatives, andsolubilizers. The solutions are filtered and filled sterile.

Suitable solvents are physiologically tolerable solvents such as water,alkanols such as ethanol, butanol, benzyl alcohol, glycerol, propyleneglycol, polyethylene glycols, N-methyl-pyrrolidone, 2-pyrrolidone, andmixtures thereof.

The active compounds can optionally be dissolved in physiologicallytolerable vegetable or synthetic oils which are suitable for injection.

Suitable solubilizers are solvents which promote the dissolution of theactive compound in the main solvent or prevent its precipitation.Examples are polyvinylpyrrolidone, polyvinyl alcohol, polyoxyethylatedcastor oil, and polyoxyethylated sorbitan ester.

Suitable preservatives are benzyl alcohol, trichlorobutanol,p-hydroxybenzoic acid esters, and n-butanol.

Oral solutions are administered directly. Concentrates are administeredorally after prior dilution to the use concentration. Oral solutions andconcentrates are prepared according to the state of the art and asdescribed above for injection solutions, sterile procedures not beingnecessary.

Solutions for use on the skin are trickled on, spread on, rubbed in,sprinkled on or sprayed on.

Solutions for use on the skin are prepared according to the state of theart and according to what is described above for injection solutions,sterile procedures not being necessary.

Further suitable solvents are polypropylene glycol, phenyl ethanol,phenoxy ethanol, ester such as ethyl or butyl acetate, benzyl benzoate,ethers such, as alkyleneglycol alkylether, e.g. dipropylenglycolmonomethylether, ketons such as acetone, methylethylketone, aromatichydrocarbons, vegetable and synthetic oils, dimethylformamide,dimethylacetamide, transcutol, solketal, propylencarbonate, and mixturesthereof.

It may be advantageous to add thickeners during preparation. Suitablethickeners are inorganic thickeners such as bentonites, colloidalsilicic acid, aluminium monostearate, organic thickeners such ascellulose derivatives, polyvinyl alcohols and their copolymers,acrylates and methacrylates.

Gels are applied to or spread on the skin or introduced into bodycavities. Gels are prepared by treating solutions which have beenprepared as described in the case of the injection solutions withsufficient thickener that a clear material having an ointment-likeconsistency results. The thickeners employed are the thickeners givenabove.

Pour-on formulations are poured or sprayed onto limited areas of theskin, the active compound penetrating the skin and acting systemically.

Pour-on formulations are prepared by dissolving, suspending oremulsifying the active compound in suitable skin-compatible solvents orsolvent mixtures. If appropriate, other auxiliaries such as colorants,bioabsorption-promoting substances, antioxidants, light stabilizers,adhesives are added.

Suitable solvents which are: water, alkanols, glycols, polyethyleneglycols, polypropylene glycols, glycerol, aromatic alcohols such asbenzyl alcohol, phenylethanol, phenoxyethanol, esters such as ethylacetate, butyl acetate, benzyl benzoate, ethers such as alkylene glycolalkyl ethers such as dipropylene glycol monomethyl ether, diethyleneglycol mono-butyl ether, ketones such as acetone, methyl ethyl ketone,cyclic carbonates such as propylene carbonate, ethylene carbonate,aromatic and/or aliphatic hydrocarbons, vegetable or synthetic oils,DMF, dimethyllacetamide, n-alkylpyrrolidones such as methylpyrrolidone,n-butylpyrrolidone or noctylpyrrolidone, N-methylpyrrolidone,2-pyrrolidone, 2,2-dimethyl-4-oxymethylene-1,3-diox-olane and glycerolformal.

Suitable colorants are all colorants permitted for use on animals andwhich can be dissolved or suspended.

Suitable absorption-promoting substances are, for example, DMSO,spreading oils such as isopropyl myristate, dipropylene glycolpelargonate, silicone oils and copolymers thereof with polyethers, fattyacid esters, triglycerides, fatty alcohols.

Suitable antioxidants are sulfites or metabisulfites such as potassiummetabisulfite, ascorbic acid, butylhydroxytoluene, butyl hydroxyanisole,tocopherol.

Suitable light stabilizers are, for example, novantisolic acid.

Suitable adhesives are, for example, cellulose derivatives, starchderivatives, polyacrylates, natural polymers such as alginates, gelatin.

Emulsions can be administered orally, dermally or as injections.

Emulsions are either of the water-in-oil type or of the oil-in-watertype.

They are prepared by dissolving the active compound either in thehydrophobic or in the hydrophilic phase and homogenizing this with thesolvent of the other phase with the aid of suitable emulsifiers and, ifappropriate, other auxiliaries such as colorants, absorption-promotingsubstances, preservatives, antioxidants, light stabilizers,viscosity-enhancing substances.

Suitable hydrophobic phases (oils) are

liquid paraffins, silicone oils, natural vegetable oils such as sesameoil, almond oil, castor oil, synthetic triglycerides such ascaprylic/capric biglyceride, triglyceride mixture with vegetable fattyacids of the chain length C₈-C₁₂ or other specially selected naturalfatty acids, partial glyceride mixtures of saturated or unsaturatedfatty acids possibly also containing hydroxyl groups, mono- anddiglycerides of the C₈-C₁₀ fatty acids,

fatty acid esters such as ethyl stearate, di-n-butyryl adipate, hexyllaurate, dipropylene glycol perlargonate, esters of a branched fattyacid of medium chain length with saturated fatty alcohols of chainlength C₁₆-C₁₈, isopropyl myristate, isopropyl palmitate,caprylic/capric acid esters of saturated fatty alcohols of chain lengthC₁₂-C₁₈, isopropyl stearate, oleyl oleate, decyl oleate, ethyl oleate,ethyl lactate, waxy fatty acid esters such as synthetic duck coccygealgland fat, dibutyl phthalate, diisopropyl adipate, and ester mixturesrelated to the latter, fatty alcohols such as isotridecyl alcohol,2-octyldodecanol, cetylstearyl alcohol, oleyl alcohol, and fatty acidssuch as oleic acid and mixtures thereof.

Suitable hydrophilic phases are: water, alcohols such as propyleneglycol, glycerol, sorbitol and mixtures thereof.

Suitable emulsifiers are:

non-ionic surfactants, e.g. polyethoxylated castor oil, polyethoxylatedsorbitan monooleate, sorbitan monostearate, glycerol monostearate,polyoxyethyl stearate, alkylphenol polyglycol ether;

ampholytic surfactants such as di-sodium N-lauryl-p-iminodipropionate orlecithin; anionic surfactants, such as sodium lauryl sulfate, fattyalcohol ether sulfates, mono/dialkyl polyglycol ether orthophosphoricacid ester monoethanolamine salt; cation-active surfactants, such ascetyltrimethylammonium chloride.

Suitable further auxiliaries are: substances which enhance the viscosityand stabilize the emulsion, such as carboxymethylcellulose,methylcellulose and other cellulose and starch derivatives,polyacrylates, alginates, gelatin, gum arabic, polyvinylpyrrolidone,polyvinyl alcohol, copolymers of methyl vinyl ether and maleicanhydride, polyethylene glycols, waxes, colloidal silicic acid ormixtures of the substances mentioned.

Suspensions can be administered orally or topically/dermally. They areprepared by suspending the active compound in a suspending agent, ifappropriate with addition of other auxiliaries such as wetting agents,colorants, bioabsorption-promoting substances, preservatives,antioxidants, light stabilizers.

Liquid suspending agents are all homogeneous solvents and solventmixtures.

Suitable wetting agents (dispersants) are the emulsifiers given above.

Other auxiliaries which may be mentioned are those given above.

Semi-solid preparations can be administered orally ortopically/dermally. They differ from the suspensions and emulsionsdescribed above only by their higher viscosity.

For the production of solid preparations, the active compound is mixedwith suitable excipients, if appropriate with addition of auxiliaries,and brought into the desired form.

Suitable excipients are all physiologically tolerable solid inertsubstances. Those used are inorganic and organic substances. Inorganicsubstances are, for example, sodium chloride, carbonates such as calciumcarbonate, hydrogencarbonates, aluminium oxides, titanium oxide, silicicacids, argillaceous earths, precipitated or colloidal silica, orphosphates. Organic substances are, for example, sugar, cellulose,foodstuffs and feeds such as milk powder, animal meal, grain meals andshreds, starches.

Suitable auxiliaries are preservatives, antioxidants, and/or colorantswhich have been mentioned above.

Other suitable auxiliaries are lubricants and glidants such as magnesiumstearate, stearic acid, talc, bentonites, disintegration-promotingsubstances such as starch or crosslinked polyvinylpyrrolidone, binderssuch as starch, gelatin or linear polyvinylpyrrolidone, and dry binderssuch as microcrystalline cellulose.

The compositions which can be used in the invention can comprisegenerally from about 0.001 to 95% of the compound of formula I.

Ready-to-use preparations contain the compounds acting againstparasites, preferably ectoparasites, in concentrations of 10 ppm to 80percent by weight, preferably from 0.1 to 65 percent by weight, morepreferably from 1 to 50 percent by weight, most preferably from 5 to 40percent by weight.

Preparations which are diluted before use contain the compounds actingagainst ectoparasites in concentrations of 0.5 to 90 percent by weight,preferably of 1 to 50 percent by weight.

Furthermore, the preparations comprise the compounds of formula Iagainst endoparasites in concentrations of 10 ppm to 2 percent byweight, preferably of 0.05 to 0.9 percent by weight, very particularlypreferably of 0.005 to 0.25 percent by weight.

The compositions comprising the compounds of formula I can be appliedorally, parenterally or topically, respectively dermally. For example,optionally the topical application is conducted in the form ofcompound-containing shaped articles such as collars, medallions, eartags, bands for fixing at body parts, and adhesive strips and foils.

Generally it is favorable to apply solid formulations which releasecompounds of formula I in total amounts of 10 mg/kg to 300 mg/kg,preferably 20 mg/kg to 200 mg/kg, most preferably 25 mg/kg to 160 mg/kgbody weight of the treated animal in the course of three weeks.

For the preparation of the shaped articles, thermoplastic and flexibleplastics as well as elastomers and thermoplastic elastomers are used.Suitable plastics and elastomers are polyvinyl resins, polyurethane,polyacrylate, epoxy resins, cellulose, cellulose derivatives, polyamidesand polyester which are sufficiently compatible with the compounds offormula I. A detailed list of plastics and elastomers as well aspreparation procedures for the shaped articles is given e.g. in WO03/086075.

The active compounds can be applied solely or in a mixture withsynergists or with other active compounds which act against pathogenicendo- and ectoparasites. For example, the active compounds of formula Ican be applied in mixtures with synthetic coccidiosis compounds,polyetherantibiotics as Amprolium, Robenidin, Toltrazuril, Monensin,Salinomycin, Maduramicin, Lasalocid, Narasin or Semduramicin or withother pesticides which are described in the list M below.

Compositions to be used according to this invention for agricultural orveterinary purposes may also contain other active ingredients, forexample other pesticides, insecticides, herbicides, fungicides,bactericides, fertilizers such as ammonium nitrate, urea, potash, andsuper-phosphate, phytotoxicants and plant growth regulators, safenersand nematicides. These additional ingredients may be used sequentiallyor in combination with the above-described compositions, if appropriatealso added only immediately prior to use (tank mix). For example, theplant(s) may be sprayed with a composition of this invention eitherbefore or after being treated with other active ingredients.

These agents can be admixed with the agents used according to theinvention in a weight ratio of 1:10 to 10:1. Mixing the compounds offormula I or the compositions comprising them in the use form aspesticides with other pesticides frequently results in a broaderpesticidal spectrum of action.

The following list M of pesticides together with which the compoundsaccording to the invention can be used and with which potentialsynergistic effects might be produced, is intended to illustrate thepossible combinations, but not to impose any limitation:

M.1. Organo(thio)phosphate compounds: acephate, azamethiphos,azinphos-ethyl, azinphos-methyl, chlorethoxyfos, chlorfenvinphos,chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos,demeton-S-methyl, diazinon, dichlorvos/DDVP, dicrotophos, dimethoate,dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur,fenamiphos, fenitrothion, fenthion, flupyrazophos, fosthiazate,heptenophos, isoxathion, malathion, mecarbam, methamidophos,methidathion, mevinphos, monocrotophos, naled, omethoate,oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate,phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos,propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos,sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos,thiometon, triazophos, trichlorfon, vamidothion;

M.2. Carbamate compounds: aldicarb, alanycarb, bendiocarb, benfuracarb,butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan,ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb,methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur,thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb, triazamate;

M.3. Pyrethroid compounds: acrinathrin, allethrin, d-cis-transallethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrinS-cylclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin,beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gammacyhalothrin,cypermethrin, alpha-cypermethrin, beta-cypermethrin, thetacypermethrin,zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin,esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate,flumethrin, taufluvalinate, halfenprox, imiprothrin, metofluthrin,permethrin, phenothrin, prallethrin, profluthrin, pyrethrin (pyrethrum),resmethrin, silafluofen, tefluthrin, tetramethrin, tralomethrin,transfluthrin;

M.4. Juvenile hormone mimics: hydroprene, kinoprene, methoprene,fenoxycarb, pyriproxyfen;

M.5. Nicotinic receptor agonists/antagonists compounds: acetamiprid,bensultap, cartap hydrochloride, clothianidin, dinotefuran,imidacloprid, thiamethoxam, nitenpyram, nicotine, spinosad (allostericagonist), spinetoram (allosteric agonist), thiacloprid, thiocyclam,thiosultap-sodium and AKD1022.

M.6. GABA gated chloride channel antagonist compounds: chlordane,endosulfan, gamma-HCH (lindane); ethiprole, fipronil, pyrafluprole,pyriprole

M.7. Chloride channel activators: abamectin, emamectin benzoate,milbemectin, lepimectin;

M.8. METI I compounds: fenazaquin, fenpyroximate, pyrimidifen,pyridaben, tebufenpyrad, tolfenpyrad, flufenerim, rotenone;

M.9. METI II and III compounds: acequinocyl, fluacyprim, hydramethylnon;

M.10. Uncouplers of oxidative phosphorylation: chlorfenapyr, DNOC;

M.11. Inhibitors of oxidative phosphorylation: azocyclotin, cyhexatin,diafenthiuron, fenbutatin oxide, propargite, tetradifon;

M.12. Moulting disruptors: cyromazine, chromafenozide, halofenozide,methoxyfenozide, tebufenozide;

M.13. Synergists: piperonyl butoxide, tribufos;

M.14. Sodium channel blocker compounds: indoxacarb, metaflumizone;

M.15. Fumigants: methyl bromide, chloropicrin sulfuryl fluoride;

M.16. Selective feeding blockers: crylotie, pymetrozine, flonicamid;

M.17. Mite growth inhibitors: clofentezine, hexythiazox, etoxazole;

M.18. Chitin synthesis inhibitors: buprofezin, bistrifluoron,chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron,hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron,triflumuron;

M.19. Lipid biosynthesis inhibitors: spirodiclofen, spiromesifen,spirotetramat;

M.20. Octapaminergic agonists: amitraz;

M.21. Ryanodine receptor modulators: flubendiamide,(R)-,(S)-3-Chlor-N-1-{2-methyl-4-[1,2,2,2-tetrafluor-1-(trifluormethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamid(M21.1)

M.22. Isoxazoline compounds:4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-N-pyridin-2-ylmethyl-benzamide(M22.1),445-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-N-(2,2,2-trifluoro-ethyl)-benzamide(M22.2),4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-N-[(2,2,2-trifluoro-ethylcarbamoyl)-methyl]-benzamide(M22.3),4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-naphthalene-1-carboxylicacid [(2,2,2-trifluoro-ethylcarbamoyl)-methyl]-amide (M22.4) and4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-N-[(methoxyimino)methyl]-2-methylbenzamide(M22.5);

M.23. Anthranilamide compounds: chloranthraniliprole, cyantraniliprole,5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid[4-cyano-2-(1-cyclopropyl-ethylcarbamoyl)-6-methyl-phenyl]-amide(M23.1), 5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid[2-chloro-4-cyano-6-(1-cyclopropyl-ethylcarbamoyl)-phenyl]-amide(M23.2), 5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid[2-bromo-4-cyano-6-(1-cyclopropyl-ethylcarbamoyl)-phenyl]-amide(M23.3),5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid[2-bromo-4-chloro-6-(1-cyclopropyl-ethylcarbamoyl)-phenyl]-amide(M23.4),5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid[2,4-dichloro-6-(1-cyclopropyl-ethylcarbamoyl)-phenyl]-amide (M23.5),5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid[4-chloro-2-(1-cyclopropyl-ethylcarbamoyl)-6-methyl-phenyl]-amide(M23.6),N′-(2-{[5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-5-chloro-3-methyl-benzoyl)-hydrazinecarboxylicacid methyl ester (M23.7),N′-(2-{[5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-5-chloro-3-methyl-benzoyl)-N′-methyl-hydrazinecarboxylicacid methyl ester (M23.8),

N′-(2-{[5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-5-chloro-3-methyl-benzoyl)-N,N′-dimethyl-hydrazinecarboxylicacid methyl ester (M23.9),N′-(3,5-Dibromo-2-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-benzoyl)-hydrazinecarboxylicacid methyl ester (M23.10),N′-(3,5-Dibromo-2-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-benzoyl)-n-methyl-hydrazinecarboxylicacid methyl ester (M23.11) andN′-(3,5-Dibromo-2-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-benzoyl)-N,N′-dimethyl-hydrazinecarboxylicacid methyl ester (M23.12);

M.24. Malononitrile compounds:2-(2,2,3,3,4,4,5,5-octafluoropentyl)-2-(3,3,3-trifluoro-propyl)malononitrile(CF₂H—CF₂—CF₂—CF₂—CH₂—C(CN)₂—CH₂—CH₂—CF₃) (M24.1) and2-(2,2,3,3,4,4,5,5-octafluoropentyl)-2-(3,3,4,4,4-pentafluorobutyl)-malonodinitrile(CF₂H—CF₂—CF₂—CF₂—CH₂—C(CN)₂—CH₂—CH₂—CF₂—CF₃) (M24.2);

M.25. Microbial disruptors: Bacillus thuringiensis subsp. Israelensi,Bacillus sphaericus, Bacillus thuringiensis subsp. Aizawai, Bacillusthuringiensis subsp. Kurstaki, Bacillus thuringiensis subsp.Tenebrionis;

M.26. Aminofuranone compounds:

-   4-{[(6-Bromopyrid-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-on    (M26.1),-   4-{[(6-Fluoropyrid-3-yl)methyl](2,2-difluoroethyl)amino}furan-2(5H)-on    (M26.2),-   4-{[(2-Chloro1,3-thiazolo-5-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-on    (M26.3),-   4-{[(6-Chloropyrid-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-on    (M26.4),-   4-{[(6-Chloropyrid-3-yl)methyl](2,2-difluoroethyl)amino}furan-2(5H)-on    (M26.5),-   4-{[(6-Chloro-5-fluoropyrid-3-yl)methyl](methyl)amino}furan-2(5H)-on    (M26.6),-   4-{[(5,6-Dichloropyrid-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-on    (M26.7),-   4-{[(6-Chloro-5-fluoropyrid-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-on    (M26.8),-   4-{[(6-Chloropyrid-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-on    (M26.9) and-   4-{[(6-Chloropyrid-3-yl)methyl](methyl)amino}furan-2(5H)-on    (M26.10);

M.27. Various compounds: aluminium phosphide, amidoflumet, benclothiaz,benzoximate, bifenazate, borax, bromopropylate, cyanide, cyenopyrafen,cyflumetofen, chinomethionate, dicofol, fluoroacetate, phosphine,pyridalyl, pyrifluquinazon, sulfur, organic sulfur compounds, tartaremetic, sulfoxaflor,N—R′-2,2-dihalo-1-R″cyclo-propanecarboxamide-2-(2,6-dichloro-α,α,α-trifluoro-ptolyl)hydrazone orN—R′-2,2-di(R′″)propionamide-2-(2,6-dichloro-α,α,α-trifluoro-p-tolyl)-hydrazone,wherein R′ is methyl or ethyl, halo is chloro or bromo, R″ is hydrogenor methyl and R′″ is methyl or ethyl,4-But-2-ynyloxy-6-(3,5-dimethyl-piperidin-1-yl)-2-fluoro-pyrimidine(M27.1), Cyclopropaneacetic acid,1,1′-[(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-4-[[(2-cyclopropylacetyl)oxy]methyl]-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-[2-hydroxy-4,6a,12b-trimethyl-11-oxo-9-(3-pyridinyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-3,6-diyl]ester(M27.2)and8-(2-Cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-aza-bicyclo[3.2.1]octane(M27.3).

The commercially available compounds of the group M may be found in ThePesticide Manual, 14th Edition, British Crop Protection Council (2006).

Paraoxon and their preparation have been described in Farm ChemicalsHandbook, Volume 88, Meister Publishing Company, 2001. Flupyrazofos hasbeen described in Pesticide Science 54, 1988, p. 237-243 and in U.S.Pat. No. 4,822,779. AKD 1022 and its preparation have been described inU.S. Pat. No. 6,300,348. The anthranilamides M23.1 to M23.6 have beendescribed in WO 2008/72743 and WO 200872783, those M23.7 to M23.12 inWO2007/043677. The phthalamide M 21.1 is known from WO 2007/101540. Thealkynylether compound M27.1 is described e.g. in JP 2006131529. Organicsulfur compounds have been described in WO 2007060839. The isoxazolinecompounds M 22.1 to M 22.5 have been described in e.g. WO2005/085216, WO2007/079162 and WO 2007/026965. The aminofuranone compounds M 26.1 to M26.10 have been described eg. in WO 2007/115644. The pyripyropenederivative M 27.2 has been described in WO 2008/66153 and WO2008/108491. The pyridazin compound M 27.3 has been described in JP2008/115155. Malononitrile compounds as those (M24.1) and (M24.2) havebeen described in WO 02/089579, WO 02/090320, WO 02/090321, WO04/006677, WO 05/068423, WO 05/068432 and WO 05/063694.

The following list of active substances, in conjunction with which thecompounds according to the invention can be used, is intended toillustrate the possible combinations but does not limit them. Fungicidalmixing partners are in particular those selected from the followinggroups:

F.I) Respiration Inhibitors

F.I-1) Inhibitors of complex III at Qo site (e.g. strobilurins)strobilurins: azoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin,kresoximmethyl, metominostrobin, orysastrobin, picoxystrobin,pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyribencarb,trifloxystrobin, methyl(2-chloro-5[1-(3-methylbenzyloxyimino)ethyl]benzyl)carbamate and 2(2-(3-(2,6-dichlorophenyl)-1-methyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino-Nmethyl-acetamide; oxazolidinediones and imidazolinones: famoxadone,fenamidone;F.I-2) Inhibitors of complex II (e.g. carboxamides):carboxanilides: benodanil, bixafen, boscalid, carboxin, fenfuram,fenhexamid, fluopyram, flutolanil, furametpyr, isopyrazam, isotianil,mepronil, oxycarboxin, penflufen, penthiopyrad, sedaxane, tecloftalam,thifluzamide, tiadinil, 2-amino-4 methyl-thiazole-5-carboxanilide,N-(3′,4′,5′ trifluorobiphenyl-2yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4 carboxamide,N-(4′-trifluoromethylthiobiphenyl-2-yl)-3 difluoromethyl-1-methyl-1Hpyrazole-4-carboxamide andN-(2-(1,3,3-trimethyl-butyl)-phenyl)-1,3-dimethyl-5 fluoro-1H-pyrazole-4carboxamide;F.I-3) Inhibitors of complex III at Qi site: cyazofamid, amisulbrom;F.I-4) Other respiration inhibitors (complex I, uncouplers)diflumetorim; tecnazen; ferimzone; ametoctradin; silthiofam;nitrophenyl derivates: binapacryl, dinobuton, dinocap, fluazinam,nitrthal-isopropyl, organometal compounds: fentin salts, such asfentin-acetate, fentin chloride or fentin hydroxide;F.II) Sterol biosynthesis inhibitors (SBI fungicides)

F.II-1) C14 demethylase inhibitors (DMI fungicides, e.g. triazoles,imidazoles) triazoles: azaconazole, bitertanol, bromuconazole,cyproconazole, difenoconazole, diniconazole, diniconazole-M,epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol,hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil,paclobutrazole, penconazole, propiconazole, prothioconazole,simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol,triticonazole, uniconazole;

imidazoles: imazalil, pefurazoate, oxpoconazole, prochloraz,triflumizole; pyrimidines, pyridines and piperazines: fenarimol,nuarimol, pyrifenox, triforine;F.II-2) Delta14-reductase inhibitors (Amines, e.g. morpholines,piperidines) morpholines: aldimorph, dodemorph, dodemorph-acetate,fenpropimorph, tridemorph;piperidines: fenpropidin, piperalin;spiroketalamines: spiroxamine;F.II-3) Inhibitors of 3-keto reductase: hydroxyanilides: fenhexamid;F.III) Nucleic acid synthesis inhibitorsF.III-1) RNA, DNA synthesisphenylamides or acyl amino acid fungicides: benalaxyl, benalaxyl-M,kiralaxyl, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl;isoxazoles and iosothiazolones: hymexazole, octhilinone;F.III-2) DNA topisomerase inhibitors: oxolinic acid;F.III-3) Nucleotide metabolism (e.g. adenosin-deaminase)hydroxy (2-amino)-pyrimidines: bupirimate;F.IV) Inhibitors of cell division and or cytoskeletonF.IV-1) Tubulin inhibitors: benzimidazoles and thiophanates: benomyl,carbendazim, fuberidazole, thiabendazole, thiophanate-methyl;triazolopyrimidines: 5-chloro-7(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5a]pyrimidineF.IV-2) Other cell division inhibitorsbenzamides and phenyl acetamides: diethofencarb, ethaboxam, pencycuron,fluopicolide, zoxamide;F.IV-3) Actin inhibitors: benzophenones: metrafenone;F.V) Inhibitors of amino acid and protein synthesisF.V-1) Methionine synthesis inhibitors (anilino-pyrimidines)anilino-pyrimidines: cyprodinil, mepanipyrim, nitrapyrin, pyrimethanil;F.V-2) Protein synthesis inhibitors (anilino-pyrimidines)antibiotics: blasticidin-S, kasugamycin, kasugamycinhydrochloride-hydrate, mildiomycin, streptomycin, oxytetracyclin,polyoxine, validamycin A;F.VI) Signal transduction inhibitorsF.VI-1) MAP/Histidine kinase inhibitors (e.g. anilino-pyrimidines)dicarboximides: fluoroimid, iprodione, procymidone, vinclozolin;phenylpyrroles: fenpiclonil, fludioxonil;F.VI-2) G protein inhibitors: quinolines: quinoxyfen;F.VII) Lipid and membrane synthesis inhibitorsF.VII-1) Phospholipid biosynthesis inhibitors organophosphoruscompounds: edifenphos, iprobenfos, pyrazophos;dithiolanes: isoprothiolane;F.VII-2) Lipid peroxidationaromatic hydrocarbons: dicloran, quintozene, tecnazene,tolclofos-methyl, biphenyl, chloroneb, etridiazole;F.VII-3) Carboxyl acid amides (CAA fungicides)cinnamic or mandelic acid amides: dimethomorph, flumorph, mandiproamid,pyrimorph;valinamide carbamates: benthiavalicarb, iprovalicarb, pyribencarb,valifenalate andN-(1-(1-(4-cyano-phenyl)ethanesulfonyl)-but-2-yl)carbamicacid-(4-fluorophenyl)ester;F.VII-4) Compounds affecting cell membrane permeability and fatty acidescarbamates: propamocarb, propamocarb-hydrochloridF.VIII) Inhibitors with Multi Site ActionF.VIII-1) Inorganic active substances: Bordeaux mixture, copper acetate,copper hydroxide, copper oxychloride, basic copper sulfate, sulfur;F.VIII-2) Thio- and dithiocarbamates: ferbam, mancozeb, maneb, metam,methasulphocarb, metiram, propineb, thiram, zineb, ziram;F.VIII-3) Organochlorine compounds (e.g. phthalimides, sulfamides,chloronitriles): anilazine, chlorothalonil, captafol, captan, folpet,dichlofluanid, dichlorophen, flusulfamide, hexachlorobenzene,pentachiorphenole and its salts, phthalide, tolylfluanid,N-(4-chloro-2-nitro-phenyl)-N-ethyl-4-methyl-benzenesulfonamide;F.VIII-4) Guanidines: guanidine, dodine, dodine free base, guazatine,guazatineacetate, iminoctadine, iminoctadine-triacetate,iminoctadine-tris(albesilate);F.VIII-5) Ahtraquinones: dithianon;F.X) Cell wall synthesis inhibitorsF.IX-1) Inhibitors of glucan synthesis: validamycin, polyoxin B;F.IX-2) Melanin synthesis inhibitors: pyroquilon, tricyclazole,carpropamide, dicyclomet, fenoxanil;F.X) Plant defence inducersF.X-1) Salicylic acid pathway: acibenzolar-5-methyl;F.X-2) Others: probenazole, isotianil, tiadinil, prohexadione-calcium;phosphonates: fosetyl, fosetyl-aluminum, phosphorous acid and its salts;F.XI) Unknown mode of action:bronopol, chinomethionat, cyflufenamid, cymoxanil, dazomet, debacarb,diclomezine, difenzoquat, difenzoquat-methylsulfate, diphenylamin,flumetover, flusulfamide, flutianil, methasulfocarb, oxin-copper,proquinazid, tebufloquin, tecloftalam, triazoxide,2-butoxy-6-iodo-3-propylchromen-4-one,N-(cyclopropylmethoxyimino-(6-difluoro-methoxy-2,3-difluoro-phenyl)-methyl)-2-phenylacetamide,N′-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-Nmethyl formamidine, N′(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methylformamidine,N′-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methylformamidine, N′-(5-difluoromethyl-2methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methylformamidine,2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazole-1-yl)-acetyl]-piperidin-4-yl}-thiazole-4-carboxylicacid methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amide,2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazole-1-yl)-acetyl]-piperidin-4-yl}-thiazole-4-carboxylicacid methyl-(R)-1,2,3,4-tetrahydro-naphthalen-1-yl-amide, methoxyaceticacid 6-tert-butyl-8-fluoro-2,3-dimethyl-quinolin-4-yl ester andN-Methyl-2-{1-[(5-methyl-3-trifluoromethyl-1H-pyrazol-1-yl)-acetyl]-piperidin-4-yl}-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-4-thiazolecarboxamide,3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin-3 yl]-pyridine,3-[5-(4-methyl-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine,5-amino-2-isopropyl-3-oxo-4-ortho-tolyl-2,3-dihydro-pyrazole-1carbothioic acid S-allyl ester,N-(6-methoxy-pyridin-3-yl)cyclopropane-carboxylic acid amide, 5-chloro-1(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1H-benzoimidazole,2-(4-chloro-phenyl)-N-[4-(3,4-dimethoxy-phenyl)-isoxazol-5-yl]-2-prop-2-ynyloxy-acetamide;F.XI) Growth regulators:abscisic acid, amidochlor, ancymidol, 6-benzylaminopurine, brassinolide,butralin, chlormequat (chlormequat chloride), choline chloride,cyclanilide, daminozide, dikegulac, dimethipin, 2,6-dimethylpuridine,ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron,gibberellic acid, inabenfide, indole-3-acetic acid, maleic hydrazide,mefluidide, mepiquat (mepiquat chloride), naphthaleneacetic acid, N 6benzyladenine, paclobutrazol, prohexadione (prohexadione-calcium),prohydrojasmon, thidiazuron, triapenthenol, tributylphosphorotrithioate, 2,3,5 tri iodobenzoic acid, trinexapac-ethyl anduniconazole;F.XII) Biological control agents

antifungal biocontrol agents: Bacillus substilis strain with NRRL No.B-21661 (e.g. RHAPSODY®, SERENADE® MAX and SERENADE® ASO from AgraQuest,Inc., USA.), Bacillus pumilus strain with NRRL No. B-30087 (e.g. SONATA®and BALLAD® Plus from AgraQuest, Inc., USA), Ulocladium oudemansii (e.g.the product BOTRY-ZEN from BotriZen Ltd., New Zealand), Chitosan (e.g.ARMOUR-ZEN from BotriZen Ltd., New Zealand).

The invertebrate pest, i.e. arthropodes and nematodes, the plant, soilor water in which the plant is growing can be contacted with thecompound(s) of formula I or the composition(s) containing them by anyapplication method known in the art. As such, “contacting” includes bothdirect contact (applying the compounds/compositions directly on theinvertebrate pest or plant—typically to the foliage, stem or roots ofthe plant) and indirect contact (applying the compounds/compositions tothe locus of the invertebrate pest or plant).

Moreover, invertebrate pests may be controlled by contacting the targetpest, its food supply, habitat, breeding ground or its locus with apesticidally effective amount of compounds of formula I. As such theapplication may be carried out before or after the infection of thelocus, growing crops, or harvested crops by the pest.

“Locus” in general means a habitat, breeding ground, cultivated plants,plant propagation material (such as seed), soil, area, material orenvironment in which a pest or parasite is growing or may grow.

In general “pesticidally effective amount” means the amount of activeingredient needed to achieve an observable effect on growth, includingthe effects of necrosis, death, retardation, prevention, and removal,destruction, or otherwise diminishing the occurrence and activity of thetarget organism. The pesticidally effective amount can vary for thevarious compounds/compositions used in the invention. A pesticidallyeffective amount of the compositions will also vary according to theprevailing conditions such as desired pesticidal effect and duration,weather, target species, locus, mode of application, and the like.

The compounds of formula I and the compositions comprising saidcompounds can be used for protecting wooden materials such as trees,board fences, sleepers, etc. and buildings such as houses, outhouses,factories, but also construction materials, furniture, leathers, fibers,vinyl articles, electric wires and cables etc. from ants and/ortermites, and for controlling ants and termites from doing harm to cropsor human being (e.g. when the pests invade into houses and publicfacilities). The compounds of formula I are applied not only to thesurrounding soil surface or into the under-floor soil in order toprotect wooden materials but it can also be applied to lumbered articlessuch as surfaces of the under-floor concrete, alcove posts, beams,plywood, furniture, etc., wooden articles such as particle boards, halfboards, etc. and vinyl articles such as coated electric wires, vinylsheets, heat insulating material such as styrene foams, etc. In case ofapplication against ants doing harm to crops or human beings, the antcontroller of the present invention is applied to the crops or thesurrounding soil, or is directly applied to the nest of ants or thelike.

The compounds of formula I can also be applied preventively to places atwhich occurrence of the pests is expected.

The compounds of formula I may also be used to protect growing plantsfrom attack or infestation by pests by contacting the plant with apesticidally effective amount of compounds of formula I. As such,“contacting the plant” includes both direct contact (applying thecompounds/compositions directly on the pest and/or plant—typically tothe foliage, stem or roots of the plant) and indirect contact (applyingthe compounds/compositions to the locus of the pest and/or plant).

In the case of soil treatment or of application to the pests dwellingplace or nest, the quantity of active ingredient ranges from 0.0001 to500 g per 100 m², preferably from 0.001 to 20 g per 100 m².

Customary application rates in the protection of materials are, forexample, from 0.01 g to 1000 g of active compound per m² treatedmaterial, desirably from 0.1 g to 50 g per m².

Insecticidal compositions for use in the impregnation of materialstypically contain from 0.001 to 95% by weight, preferably from 0.1 to45% by weight, and more preferably from 1 to 25% by weight of at leastone repellent and/or insecticide.

For use in bait compositions, the typical content of active ingredientis from 0.001% by weight to 15% by weight, desirably from 0.001% byweight to 5% by weight of active compound.

For use in spray compositions, the content of active ingredient is from0.001 to 80% by weight, preferably from 0.01 to 50% by weight and mostpreferably from 0.01 to 15% by weight.

For use in treating crop plants, the rate of application of the activeingredients of this invention may be in the range of 0.1 g to 4000 g perhectare, desirably from 5 g to 600 g per hectare, more desirably from 10g to 300 g per hectare.

In the treatment of seed, the application rates of the activeingredients are generally from 0.1 g to 10 kg per 100 kg of seed,preferably from 1 g to 1 kg per 100 kg of seed, in particular from 1 gto 250 g per 100 kg of seed, in particular from 50 g to 150 g per 100 kgof seed.

The present invention is now illustrated in further detail by thefollowing examples which are not intended to limit the invention tothem.

I. PREPARATION EXAMPLES

Products were characterized by HPLC (High Performance LiquidChromatography Mass Spectrometry). HPLC was carried out using ananalytic RP-18 column (Chromolith Speed ROD from Merck KgaA, Germany)which was operated at 40° C. Acetonitrile with 0.1% by volume of atrifluoroacetic acid/water mixture and 0.1% by volume of trifluoroaceticacid served as mobile phase; flow rate: 1.8 mL/min and injection volume:2 μl.

Example 1[2-(4-Chloro-phenyl)-7-trifluoromethyl-quinazolin-4-yl]ethylamine (I-99)

1.1 2-(4-Chlorophenyl)-7-trifluoromethyl-3H-quinazolin-4-one:

To a stirred suspension of 2-amino-4-(trifluoromethyl)benzamide (33.6 g,0.16 mol) in water (750 mL) was added dropwise 4-chlorobenzaldehyde.Iron trichloride hexahydrate (133 g) was then added in portions. Thereaction mixture was then heated at reflux for 24 h. After allowing thesuspension to cool to room temperature, the precipitate was isolated byvacuum filtration washing with water (3×500 mL) and dried under vacuum(10 mbar, 50° C.). Yield=50 g, 94%; HPLC-mass spectrometry (LC-MS): 3.7min, 325 (M⁺).

1.2 4-Chloro-2-(4-chloro-phenyl)-7-trifluoromethylquinazoline

To a stirred suspension of2-(4-chlorophenyl)-7-trifluoromethyl-3H-quinazolin-4-one (50 g, 0.15mol) in dioxane (400 mL) was added dropwise phosphorus oxychloride (43mL, 0.46 mol). The suspension was then heated at reflux for 2 h thenallowed to cool to room temperature and evaporated under reducedpressure. The remaining solid was dissolved in dioxane (1 L) and anaqueous solution of sodium hydroxide (50 mL, 10% weight/weight (w/w))was added dropwise maintaining the internal temperature≦10° C.). Water(1 L) was then added to the resultant suspension followed by thedropwise addition of a further quantity of aqueous sodium hydroxide (90mL, 10% w/w). The precipitate was isolated by vacuum filtration washingwith water (3×500 mL) and dried under vacuum (10 mbar, 50° C.). Yield=49g, 93%; LC-MS: 4.7 min, 343 (M⁺); ¹H NMR (dimethylsulfoxide (DMSO)-d₆) δ7.68 (d, 2H, J=8.9 Hz), 8.12 (dd, 1H, J=8.9, 1.8 Hz), 8.48-8.54 (m, 4H).

1.3 [2-(4-Chloro-phenyl)-7-trifluoromethyl-quinazolin-4-yl]ethylamine

To a stirred solution of4-chloro-2-(4-chloro-phenyl)-7-trifluoromethylquinazoline (52.0 g, 0.15mol) in THF (400 mL) at 0° C. was added dropwise a solution ofethylamine (0.45 mol, 230 mL, 2 M in THF. The ice-bath was then removedand the reaction mixture was allowed to stir at room temperature for 1h. The reaction mixture was concentrated under reduced pressure thenpartitioned between ethyl acetate (400 mL) and water (400 mL) removingany undissolved solid by vacuum filtration. The filtrate wasconcentrated to approximately 200 mL and the resultant precipitate wasremoved by vacuum filtration. The filtrate was again concentrated toapproximately 100 mL volume and the resultant precipitate was removed byvacuum filtration. Finally the filtrate was cooled to 0° C. upon which[2-(4-chloro-phenyl)-7-trifluoromethyl-quinazolin-4-yl]ethylamineprecipitated from solution. The precipitate (30 g) was isolated byvacuum filtration and dried under vacuum (10 mbar, 50° C.). A secondamount of the precipitate of equal purity (19.6 g) was obtainedfollowing concentration of the filtrate to approximately 50 mL volume,cooling to 0° C., filtration and drying under vacuum. Combinedyield=49.6 g, 93%; LC-MS: 2.9 min, 352 (M⁺); ¹H NMR (DMSO-d₆): δ 1.38(t, 1H, J=7 Hz), 3.77-3.85 (m, 2H), 7.46 (d, 2H, J=8.7 Hz), 7.64 (dd,1H, J=8.3, 1.8 Hz), 7.72-7.78 (br s, 1H), 8.09 (s, 1H), 8.17 (d, 1H,J=8.3 Hz), 8.59 (d, 2H, J=8.7 Hz).

Example 2[2-(4-Trifluoromethylphenyl)-7-trifluoromethyl-quinazolin-4-yl]ethylamine(I-209)

2.1 7-Trifluoromethyl-1H-quinazoline-2,4-dione

2-Amino-4-trifluoromethylbenzoic acid (25.0 g, 122 mmol) and urea (75.0g, 1.2 mol) were combined and heated at 200° C. while stirring. After 1h, the reaction mixture was allowed to cool to 100° C. and water (100mL) was added. The reaction mixture was then allowed to cool to roomtemperature and the solid was isolated by vacuum filtration washing withwater (500 mL). The solid was then dried under vacuum (10 mbar, 50° C.).Yield=24 g, 86%; LC-MS: 2.1 min, 230 (M⁺); ¹H NMR (DMSO-d₆) δ 7.44 (s,1H) 7.47 (d, 1H), 8.07 (d, 1H), 11.43 (br s, 1H), 11.56 (br s, 1H).

2.2 (2-Chloro-7-trifluoromethyl-quinazolin-4-yl)ethylamine

To a stirred suspension of 7-trifluoromethyl-1H-quinazoline-2,4-dione(25 g, 0.11 mol) and N,N-dimethylaniline (13.1 g, 0.11 mol) at 0° C. wasadded phosphorus oxychloride (101 mL, 1.1 mol) and the reaction mixturewas heated at reflux for 6 h. The reaction mixture was allowed to coolto room temperature then concentrated under reduced pressure. Theresultant solid was dissolved in THF (50 mL) then cooled to 0° C. and asolution of ethylamine (10 mL, 2 molar in THF) was added dropwise withstirring. After 2 h, the reaction mixture was concentrated under reducedpressure, diluted with water (250 mL) and extracted with ethyl acetate(2×150 mL). The combined organic layers were dried over MgSO₄, filteredand concentrated under reduced pressure. Yield=14 g, 47%; LC-MS: 3.1min, 276 (M⁺); ¹H NMR (DMSO-d₆): δ 1.26 (apparent t, 3H, J=7 Hz), 3.57(ddd, 2H, J=12.7, 7.3, 5.6 Hz), 7.84 (dd, 1H, J=8.7, 1.6 Hz), 7.93 (s,1H), 8.49 (d, 1H, J=8.7 Hz), 9.05 (apparent t, 1H, J=5 Hz).

2.3[2-(4-Trifluoromethylphenyl)-7-trifluoromethyl-quinazolin-4-yl]ethylamine

A solution of (2-chloro-7-trifluoromethyl-quinazolin-4-yl)ethylamine(276 mg, 1.00 mmol), p-trifluoromethylphenylboronic acid (285 mg, 1.50mmol), tetrakis(triphenylphosphine)palladium (116 mg, 0.10 mmol) andsodium carbonate (0.21 g, 2.0 mmol) in dimethoxyethane/water (3 mL, 2:1)was heated at 80° C. for 16 h. The reaction mixture was thenconcentrated under reduced pressure, diluted with water (50 mL) andextracted with CH₂Cl₂ (3×25 mL). The combined organic layers were driedover MgSO₄, filtered, and concentrated under reduced pressure.Purification by flash chromatography using cyclohexane:ethyl acetate(4:1) as solvent afforded[2-(4-trifluoromethylphenyl)-7-trifluoromethyl-quinazolin-4-yl]ethylamine.Yield=0.20 g, 52%; LC-MS: 3.2 min, 385 (M⁺); ¹H NMR (DMSO-d₆): δ 1.34(t, 3H, J=7.2 Hz), 3.68-3-78 (m, 2H), 7.82 (dd, 1H, J=8.6, 1.7 Hz), 7.88(d, 2H, J=8.1 Hz), 8.07 (s, 1H), 8.50 (d, 1H, J=8.6 Hz), 8.67 (d, 2H,J=8.1 Hz), 8.70-8.76 (m, 1H).

Example 3[2-(4-Chlorophenyl)-5,6,difluoro-7-trifluoromethylquinazolin-4-yl]ethylamine(I-401)

3.1 2,3-Difluoro-6-iodo-4-trifluoromethylbenzoic acid

A suspension of 2,3-difluoro-4-trifluoromethylbenzoic acid (1.00 g, 4.42mmol), palladium (II) acetate (0.199 g, 0.88 mmol) and N-iodosuccinimide(1.19 g, 5.31 mmol) in dimethylformamide (10 mL) were heated at 100° C.for 2 d. The reaction mixture was then concentrated under reducedpressure, diluted with ethyl acetate (100 mL) and washed with water(3×25 mL). The organic layer was dried over MgSO₄, filtered andconcentrated under reduced pressure to afford a brown solid (1.53) gwhich was used without further purification. LC-MS: 2.6 min, 353 (M⁺).

3.22-(4-Chlorophenyl)-5,6-difluoro-7-trifluoromethyl-3H-quinazolin-4-one

A suspension of crude 2,3-difluoro-6-iodo-4-trifluoromethylbenzoic acid(1.00 g), 4-chlorobenzamide hydrochloride (0.814 g, 4.26 mmol), copper(I) iodide (0.108 g), caesium carbonate (1.85 g, 5.68 mmol) indimethylformamide (8 mL) were stirred under nitrogen at room temperaturefor 1 week. The reaction mixture was then diluted with ethyl acetate(100 mL) and washed with hydrochloric acid (1 M, 25 mL) and water (25mL). The organic phase was dried over MgSO₄, filtered and concentratedunder reduced pressure (0.98 g). The reaction was repeated with crude2,3-difluoro-6-iodo-4-trifluoromethylbenzoic acid (0.50 g) to afford anadditional portion (0.57 g) of the quinazolin-4-one. LC-MS: 3.6 min, 361(M⁺).

3.34-chloro-2-(4-chlorophenyl)-5,6-difluoro-7-trifluoromethylquinazoline

To a suspension of the above quinazolin-4-one (1.50 g) in dioxane (45mL) was added phosphorus oxychloride (3.9 mL, 41 mmol) and the resultantsolution was heated at reflux for 16 h. The reaction mixture was thenconcentrated under reduced pressure to afford a gummy solid which wasused without further purification.

3.4[2-(4-Trifluoromethylphenyl)-5,6,difluoro-7-trifluoromethylquinazolin-4-yl]ethylamine

A suspension of the above crude quinazoline and ethylamine (2 M in THF,25 mL) was stirred at room temperature for 16 h. The reaction mixturewas then concentrated under reduced pressure, diluted with ethyl acetate(75 mL) and washed with water (25 mL), aqueous sodium carbonate (25 mL)and water (25 mL). The organic phase was dried over MgSO₄, filtered andconcentrated under reduced pressure to afford a crystalline solid.Recrystallization from hot cyclohexane:ethyl acetate (4:1) afforded[2-(4-chlorophenyl)-5,6,difluoro-7-trifluoromethylquinazolin-4-yl)ethylamine.Yield=0.10 g, 6% over 4 steps. LC-MS: 4.6 min, 388 (M⁺); ¹H NMR(tetrahydrofuran (THF)-d₆): δ 1.38 (apparent t, J=7 Hz, 3H), 3.79-3.87(m, 2H), 7.47 (apparent d, J=8.8 Hz, 2H), 7.51-7.59 (broad s, 1H), 7.96(dd, J=6.2, 1.4 Hz, 1H), 8.54 (apparent d, J=8.8 Hz, 2H).

Compounds of formula I prepared according to the above mentioned methodtogether with their physico-chemical data are compiled below in TablesE, F and G. The corresponding physico-chemical data (LC/MS) whereint_(R) is retention time in minutes and M is the mass of respectivemolecular ion are listed in the Tables.

In Table E, compounds are of the general formula:

wherein R^(E) is a mono- or dialkylamino derivative:

-   -   R^(E) is

and # denotes the binding site to the remainder

TABLE E I R^(E) LC/MS I-1

t_(R:): 3.751′ M = 470.9 I-2

t_(R:): 3.672′ M = 437.9 I-3

t_(R:): 3.591′ M = 451.9 I-4

t_(R:): 3.742′ M = 437.9 I-5

t_(R:): 2.532′ M = 380.8 I-6

t_(R:): 3.057′ M = 439.9 I-7

t_(R:): 4.068′ M = 447.9 I-8 cyclopropylamino t_(R:): 3.183′ M = 364.1I-9

t_(R:): 3.678′ M = 461.6 I-10 cyclopentylamino t_(R:): 3.421′ M = 391.8I-11 #-CH₂CH₂OCH₂CH₃ t_(R:): 3.073′ M = 396.0 I-12

t_(R:): 3.464′ M = 440.0 I-13

t_(R:): 3.083′ M = 410.0 I-14

t_(R:): 2.507′ M = 409.1 I-15

t_(R:): 4.063′ M = 418.8 I-16

t_(R:): 3.355′ M = 389.8 I-17

t_(R:): 3.592′ M = 407.8 I-18

t_(R:): 3.91′ M = 404.8 I-19

t_(R:): 2.974′ M = 429.8 I-20

t_(R:): 4.559′ M = 393.8 I-21

t_(R:): 3.395′ M = 423.8 I-22

t_(R:): 4.275′ M = 459.9 I-23

t_(R:): 3.286′ M = 379.8 I-24

t_(R:): 3.812′ M = 465.9 I-25

t_(R:): 3.932′ M = 451.9 I-26

t_(R:): 3.174′ M = 423.8 I-27

t_(R:): 2.746′ M = 379.8 I-28 benzyl t_(R:): 3.520′ M = 414.1 I-29propyl t_(R:): 3.330′ M = 366.1 I-30 cyclohexyl t_(R:): 3.524′ M = 406.0I-31 #-CH₂C(CH₃)₃ t_(R:): 3.461′ M = 394.1 I-32

t_(R:): 3.541′ M = 439.0 I-33

t_(R:): 2.731′ M = 396.0 I-34

t_(R:): 3.908′ M = 436.1 I-35

t_(R:): 2.831′ M = 451.1 I-36

t_(R:): 2.560′ M = 409.0 I-37

t_(R:): 3.457′ M = 394.0 I-38 #-CH₂CH₂OCH₃ t_(R:): 2.897′ M = 382.0 I-39

t_(R:): 3.201′ M = 495.1 I-40

t_(R:): 3.796′ M = 439.9 I-41

t_(R:): 3.499′ M = 441.9 I-42

t_(R:): 3.584′ M = 390.8 I-43

t_(R:): 3.415′ M = 451.9 I-44

t_(R:): 3.755′ M = 455.9 I-45

t_(R:): 2.881′ M = 436.9 I-46 #-CH₂cyclopentyl t_(R:): 3.437′ M = 405.8I-47

t_(R:): 3.442′ M = 405.9 I-48

t_(R:): 3.383′ M = 433.9 I-49

t_(R:): 3.711′ M = 390.8 I-50

t_(R:): 3.816′ M = 455.9 I-51

t_(R:): 3.821′ M = 433.8 I-52

t_(R:): 4.003′ M = 390.7 I-53

t_(R:): 3.968′ M = 403.8 I-54

t_(R:): 3.862′ M = 433.9 I-55

t_(R:): 4.333′ M = 510.1 I-56

t_(R:): 3.176′ M = 398.0 I-57

t_(R:): 2.885′ M = 424.0 I-58

t_(R:): 3.645′ M = 425.9 I-59

t_(R:): 3.794′ M = 435.9 I-60

t_(R:): 3.593′ M = 421.9 I-61

t_(R:): 3.358′ M = 393.8 I-62

t_(R:): 3.704′ M = 407.9 I-63

t_(R:): 3.021′ M = 409.8 I-64

t_(R:): 3.54′ M = 453.9 I-65

t_(R:): 2.83′ M = 448.9 I-66

t_(R:): 3.551′ M = 437.8 I-67

t_(R:): 3.292′ M = 437.8 I-68

t_(R:): 2.895′ M = 465.9 I-69

t_(R:): 4.078′ M = 471.9 I-70

t_(R:): 4.222′ M = 461.9 I-71 #-NCH₂cyclopropyl t_(R:): 3.214′ M = 378.0I-72

t_(R:): 3.646′ M = 408.1 I-73

t_(R:): 3.328′ M = 380.0 I-74

t_(R:): 3.624′ M = 408.1 I-75 #-N-cyclobutyl t_(R:): 3.272′ M = 378.0I-76 #-NH₂ t_(R:): 2.652′ M = 324.0 I-77

t_(R:): 3.417′ M = 394.0 I-78 #-N-allyl t_(R:): 3.116′ M = 364.0 I-79

t_(R:): 3.359′ M = 440.0 I-80

t_(R:): 2.978′ M = 396.0 I-81

t_(R:): 2.801′ M = 394.0 I-82

t_(R:): 3.028′ M = 426.0 I-83

t_(R:): 2.920′ M = 412.0 I-84

t_(R:): 3.389′ M = 451.9 I-85

t_(R:): 3.422′ M = 393.8 I-86

t_(R:): 3.725′ M = 433.9 I-87

t_(R:): 3.432′ M = 427.) I-88

t_(R:): 3.443′ M = 446./ I-89

t_(R:): 3.025′ M = 393.8 I-90

t_(R:): 4.21′ M = 353.7 I-91

t_(R:): 3.088′ M = 409.7 I-92

t_(R:): 3.529′ M = 421.9 I-93

t_(R:): 3.9′ M = 451.9 I-94

t_(R:): 3.519′ M = 391.8 I-95

t_(R:): 3.069′ M = 409.8 I-96

t_(R:): 3.29′ M = 465.9 I-97

t_(R:): 3.795′ M = 451.9 I-98

t_(R:): 2.66′ M = 409.8 I-99

t_(R:): 3.130′ M = 352.1 I-100

t_(R:): 3.357′ M = 380.0 I-101

t_(R:): 3.298′ M = 380.0 I-102

t_(R:): 3.527′ M = 394.0 I-103

t_(R:): 2.800′ M = 410.0 I-104

t_(R:): 2.586′ M = 421.0 I-105

t_(R:): 2.508′ M = 437.0 I-106

t_(R:): 2.841′ M = 424.0 I-107

t_(R:): 2.561′ M = 423.1 I-108

t_(R:): 3.933′ M = 404.8 I-109

t_(R:): 3.209′ M = 409.8 I-110

t_(R:): 2.945′ M = 338.1 I-111

t_(R:): 3.280′ M = 366.1 I-112

t_(R:): 3.48′ M = 395.8 I-113

t_(R:): 3.713′ M = 420.1 I-114

t_(R:): 2.888′ M = 370.0 I-115

t_(R:): 3.533′ M = 437.8 I-116

t_(R:): 3.404′ M = 509.1 I-117

t_(R:): 3.040′ M = 408.0 I-118

t_(R:): 3.492′ M = 408.1 I-119

t_(R:): 3.217′ M = 412.0 I-120

t_(R:): 3.101′ M = 400.0 I-121

t_(R:): 3.043′ M = 410.0 I-122

t_(R:): 3.528′ M = 404.8 I-123

t_(R:): 3.489′ M = 407.9 I-124

t_(R:): 2.772′ M = 395.8 I-125

t_(R:): 3.682′ M = 417.9 I-126

t_(R:): 3.207′ M = 480.9 I-127

t_(R:): 3.388′ M = 379.8 I-128

t_(R:): 3.485′ M = 451.9 I-129

t_(R:): 3.209′ M = 409.8 I-130

t_(R:): 2.585′ M = 450.9 I-131

t_(R:): 3.207′ M = 411.9 I-132

t_(R:): 2.675′ M = 422.8 I-133

t_(R:): 3.295′ M = 391.8 I-134

t_(R:): 3.743′ M = 407.8 I-135

t_(R:): 4.034′ M = 441.8 I-136

t_(R:): 3.551′ M = 417.9 I-137

t_(R:): 3.721′ M = 389.8 I-138

t_(R:): 3.509′ M = 441.8 I-139

t_(R:): 3.833′ M = 463.93 I-140

t_(R:): 3.896′ M = 463.9 I-141

t_(R:): 3.038′ M = 425.8 I-142

t_(R:): 3.073′ M = 409.8 I-143

t_(R:): 3.219′ M = 467.9 I-144

t_(R:): 3.619′ M = 493.9 I-145

t_(R:): 3.271′ M = 465.9 I-146

t_(R:): 4.146′ M = 491.9 I-147

t_(R:): 3.632′ M = 414.3 I-148

t_(R:): 3.562′ M = 410.2 I-149

t_(R:): 3.932′ M = 493.9 I-150

t_(R:): 2.663′ M = 465.9 I-151

t_(R:): 3.392′ M = 388.0 I-152

t_(R:): 3.428′ M = 420.0 I-153

t_(R:): 3.308′ M = 420.0 I-154

t_(R:): 3.807′ M = 406.0 I-155

t_(R:): 3.700′ M = 432.1 I-156

t_(R:): 2.471′ M = 395.0 I-157

t_(R:): 3.482′ M = 394.0 I-158

t_(R:): 3.152′ M = 455.9 I-159

t_(R:): 3.972′ M = 419.7 I-160

t_(R:): 3.552′ M = 391.8 I-161

t_(R:): 3.558′ M = 441.9 I-162

t_(R:): 3.296′ M = 391.8 I-163

t_(R:): 3.397′ M = 433.9 I-164

t_(R:): 3.49′ M = 453.9 I-165

t_(R:): 3.432′ M = 405.85 I-166

t_(R:): 3.331′ M = 456.9 I-167

t_(R:): 3.221′ M = 409.8 I-168

t_(R:): 3.165′ M = 409.8 I-169

t_(R:): 3.855′ M = 377.8 I-170

t_(R:): 3.298′ M = 391.8 I-171

t_(R:): 3.823′ M = 395.8 I-172

t_(R:): 3.911′ M = 437.8 I-173

t_(R:): 3.402′ M = 465.9 I-174

t_(R:): 4.207′ M = 479.9 I-175

t_(R:): 3.181′ M = 423.8 I-176

t_(R:): 3.204′ M = 409.8 I-177

t_(R:): 3.463′ M = 398.2 I-178

t_(R:): 3.075′ M = 425.8 I-179

t_(R:): 3.609′ M = 423.82 I-180

t_(R:): 3.733′ M = 479.9 I-181

t_(R:): 4.32′ M = 461.9 I-182

t_(R:): 3.434′ M = 375.8 I-183

t_(R:): 3.74′ M = 479.9 I-184

t_(R:): 3.776′ M = 479.9 I-185

t_(R:): 3.471′ M = 423.9 I-186

t_(R:): 3.518′ M = 391.8 I-187

t_(R:): 3.894′ M = 455.9 I-188

t_(R:): 2.469′ M = 410.8 I-189

t_(R:): 2.469′ M = 410.8 I-190

t_(R:): 3.699′ M = 414.3 I-191

t_(R:): 3.224′ M = 395.8 I-192

t_(R:): 3.253′ M = 376.8 I-193

t_(R:): 3.331′ M = 361.7 I-194

t_(R:): 3.188′ M = 404.0 I-195

t_(R:): 3.452′ M = 394.0 I-196

t_(R:): 3.132′ M = 438.0 I-197

t_(R:): 3.698′ M = 407.9 I-198

t_(R:): 3.882′ M = 417.9 I-199

t_(R:): 4.081′ M = 445.9 I-200

t_(R:): 3.755′ M = 407.9

In Table F, compounds are of the general formula:

wherein R^(F) in the above formula is R¹ or R²and R^(F) is a propyl (Pr) or an ethyl (Et) and A as indicated in TableF:

TABLE F I R^(F) A LC/MS I-201 Et

t_(R): 2.654′ M = 335.8 I-202 Et

t_(R): 3.123′ M = 398.1 I-203 Et

t_(R): 3.404′ M = 387.0 I-204 Pr

t_(R): 3.613′ M = 401.0 I-205 Pr

t_(R): 2.778′ M = 428.8 I-206 Et

t_(R): 2.922′ M = 414.2 I-207 Pr

t_(R): 3.213′ M = 428.2 I-208 Et

t_(R): 3.109′ M = 363.0 I-209 Et

t_(R): 3.239′ M = 386.0 I-210 Et

t_(R): 3.255′ M = 410.1 I-211 Et

t_(R): 3.396′ M = 454.0 I-212 Et

t_(R): 3.147′ M = 404.0 I-213 Et

t_(R): 3.281′ M = 420.0 I-214 Et

t_(R): 2.461′ M = 333.1 I-215 Et

t_(R): 3.598′ M = 420.0 I-216 Et

t_(R): 2.778′ M = 429.0 I-217 Et

t_(R): 3.29′ M = 419.8 I-218 Et

t_(R): 2.981′ M = 369.8 I-219 Pr

t_(R): 3.183′ M = 383.8 I-220 Et

t_(R): 3.101′ M = 386.2 I-221 Pr

t_(R): 3.279′ M = 400.2 I-222 Et

t_(R): 3.35′ M = 369.8 I-223 Pr

t_(R): 3.564′ M = 383.8 I-224 Et

t_(R): 3.562′ M = 386.2 I-225 Pr

t_(R): 3.755′ M = 400.2 I-226 Et

t_(R): 3.016′ M = 374.4 I-227 Pr

t_(R): 3.201′ M = 388.4 I-228 Et

t_(R): 3.246′ M = 369.8 I-229 Pr

t_(R): 3.441′ M = 383.8 I-230 Et

t_(R): 3.05′ M = 353.3 I-231 Pr

t_(R): 3.251′ M = 367.3 I-232 Et

t_(R): 2.735′ M = 397.9 I-233 Pr

t_(R): 3.968′ M = 417.3 I-234 Et

t_(R): 3.789′ M = 403.3 I-235 Pr

t_(R): 2.945′ M = 367.6 I-236 Et

t_(R): 2.768′ M = 353.3 I-237 Pr

t_(R): 3.052′ M = 411.2 I-238 Et

t_(R): 2.885′ M = 369.8 I-239 Pr

t_(R): 3.078′ M = 383.8 I-240 Et

t_(R): 3.024′ M = 403.3 I-241 Pr

t_(R): 3.199′ M = 417.3 I-242 Pr

t_(R): 2.884′ M = 346.4 I-243 Et

t_(R): 2.706′ M = 332.3 I-244 Pr

t_(R): 3.377′ M = 416.4 I-245 Pr

t_(R): 3.6′ M = 416.4 I-246 Pr

t_(R): 3.6′ M = 448.8 I-247 Pr

t_(R): 3.295′ M = 414.4 I-248 Pr

t_(R): 3.458′ M = 428.4 I-249 Pr

t_(R): 3.423′ M = 448.8 I-250 Pr

t_(R): 3.125′ M = 412.4 I-251 Pr

t_(R): 3.594′ M = 430.4 I-252 Pr

t_(R): 3.798′ M = 456.5 I-253 Pr

t_(R): 3.252′ M = 426.4 I-254 Pr

t_(R): 3.227′ M = 402.4 I-255 Et

t_(R): 4.007′ M = 419.8 I-256 Pr

t_(R): 4.146′ M = 433.8 I-257 Et

t_(R): 4.094′ M = 454.2 I-258 Et

t_(R): 4.252′ M = 387.7 I-259 Et

t_(R): 4.044′ M = 371.3 I-260 Pr

t_(R): 4.283′ M = 385.3 I-261 Et

t_(R): 3.047′ M = 365.8 I-262 Et

t_(R): 3.577′ M = 387.7 I-263 Pr

t_(R): 3.749′ M = 401.8 I-264 Pr

t_(R): 3.223′ M = 379.8 I-265 Pr

t_(R): 4.456′ M = 401.8 I-266 Et

t_(R): 3.131′ M = 371.3 I-267 Pr

t_(R): 3.353′ M = 385.3 I-268 Pr

t_(R): 3.596′ M = 441.4 I-269 Pr

t_(R): 3.507′ M = 401.8 I-270 Pr

t_(R): 3.513′ M = 415.3 I-271 Pr

t_(R): 3.323′ M = 359.3 I-272 Pr

t_(R): 3.25′ M = 375.4 I-273 Pr

t_(R): 3.396′ M = 391.4 I-274 Pr

t_(R): 2.655′ M = 438.5 I-275 Pr

t_(R): 2.98′ M = 457.5 I-276 Pr

t_(R): 2.878′ M = 413.4 I-277 Pr

t_(R): 2.833′ M = 409.4 I-278 Pr

t_(R): 2.684′ M = 414.4 I-279 Pr

t_(R): 2.493′ M = 404.4 I-280 Pr

t_(R): 2.401′ M = 374.4 I-281 Pr

t_(R): 2.508′ M = 388.4 I-282 Pr

t_(R): 3.139′ M = 389.4 I-283 Pr

t_(R): 2.709′ M = 424.4 I-284 Pr

t_(R): 2.674′ M = 388.4 I-285 Pr

t_(R): 2.597′ M = 402.4 I-286 Pr

t_(R): 2.65′ M = 402.4 I-287 Pr

t_(R): 2.829′ M = 416.4 I-288 Pr

t_(R): 2.958′ M = 373.4 I-289 Pr

t_(R): 2.983′ M = 423.4 I-290 Pr

t_(R): 3.219′ M = 377.4 I-291 Pr

t_(R): 3.111′ M = 345.4 I-292 Pr

t_(R): 3.036′ M = 361.4 I-293 Pr

t_(R): 3.624′ M = 441.4 I-294 Pr

t_(R): 3.767′ M = 437.5 I-295 Pr

t_(R): 3.192′ M = 356.3 I-296 Pr

t_(R): 3.513′ M = 468.4 I-297 Pr

t_(R): 3.508′ M = 441.4 I-298 Pr

t_(R): 3.847′ M = 491.4 I-299 Pr

t_(R): 3.528′ M = 453.5 I-300 Pr

t_(R): 3.561′ M = 453.5 I-301 Pr

t_(R): 3.473′ M = 453.5 I-302 Pr

t_(R): 3.791′ M = 491.4 I-303 Pr

t_(R): 3.86′ M = 507.4 I-304 Pr

t_(R): 3.83′ M = 507.4 I-305 Et

t_(R): 3.308′ M = 387.7 I-306 Pr

t_(R): 3.458′ M = 422.4 I-307 Pr

t_(R): 3.237′ M = 428.5 I-308 Pr

t_(R): 3.083′ M = 413.4 I-309 Pr

t_(R): 2.942′ M = 398.4 I-310 Pr

t_(R): 3.523′ M = 465.4 I-311 Pr

t_(R): 3.121′ M = 398.4 I-312 Pr

t_(R): 2.695′ M = 398.4 I-313 Pr

t_(R): 3.359′ M = 397.4 I-314 Pr

t_(R): 2.731′ M = 431.4 I-315 Et

t_(R): 3.294′ M = 402.4 I-316 Et

t_(R): 3.075′ M = 388.4 I-317 Pr

t_(R): 2.611′ M = 415.4 I-318 Pr

t_(R): 3.184′ M = 401.4 I-319 Pr

t_(R): 3.188′ M = 473.5 I-320 Pr

t_(R): 3.532′ M = 449.5 I-321 Pr

t_(R): 3.501′ M = 397.4 I-322 Pr

t_(R): 2.183′ M = 397.4 I-323 Pr

t_(R): 3.076′ M = 425.5 I-324 Pr

t_(R): 2.668′ M = 440.4 I-325 Pr

t_(R): 3.067′ M = 491.5 I-326 Pr

t_(R): 2.922′ M = 457.5 I-327 Pr

t_(R): 2.876′ M = 411.4 I-328 Pr

t_(R): 2.876′ M = 411.4 I-329 Pr

t_(R): 2.282′ M = 417.4 I-330 Pr

t_(R): 2.132′ M = 403.4 I-331 Pr

t_(R): 2.46′ M = 431.5 I-332 Pr

t_(R): 2.476′ M = 431.5 I-333 Pr

t_(R): 2.597′ M = 445.5 I-334 Pr

t_(R): 2.334′ M = 478.4 I-335 Pr

t_(R): 2.678′ M = 347.3 I-336 Pr

t_(R): 2.867′ M = 331.3 I-337 Pr

t_(R): 3.392′ M = 427.5 I-338 Pr

t_(R): 2.763′ M = 465.5 I-339 Pr

t_(R): 2.182′ M = 419.4 I-340 Pr

t_(R): 2.527′ M = 424.4 I-341 Pr

t_(R): 3.043′ M = 498.4 I-342 Pr

t_(R): 2.994′ M = 375.4 I-343 Pr

t_(R): 4.077′ M = 365.3 I-344 Pr

t_(R): 3.11′ M = 373.4 I-345 Pr

t_(R): 3.161′ M = 370.4 I-346 Pr

t_(R): 2.679′ M = 371.4 I-347 Pr

t_(R): 2.337′ M = 478.5 I-348 Pr

t_(R): 2.995′ M = 483.5 I-349 Pr

t_(R): 2.804′ M = 478.5 I-350 Pr

t_(R): 2.974′ M = 397.4 I-351 Pr

t_(R): 3.144′ M = 472.5 I-352 Pr

t_(R): 3.062′ M = 498.4 I-353 Pr

t_(R): 3.225′ M = 492.5 I-354 Pr

t_(R): 2.843′ M = 444.5 I-355 Pr

t_(R): 3.483′ M = 390.4 I-356 Pr

t_(R): 2.749′ M = 388.4 I-357 Pr

t_(R): 4.394′ M = 400.2 I-358 Pr

t_(R): 4.769′ M = 467.3 I-359 Pr

t_(R): 2.96′ M = 345.4 I-360 Pr

t_(R): 2.794′ M = 444.5 I-361 Pr

t_(R): 3.18′ M = 492.5 I-362 Pr

t_(R): 2.789′ M = 456.5 I-363 Pr

t_(R): 3.094′ M = 472.5 I-364 Pr

t_(R): 2.751′ M = 409.4 I-365 Pr

t_(R): 3.27′ M = 460.5 I-366 Pr

t_(R): 3.155′ M = 357.3 I-367 Pr

t_(R): 3.697′ M = 505.5 I-368 Pr

t_(R): 3.222′ M = 497.3 I-369 Pr

t_(R): 3.199′ M = 450.3 I-370 Pr

t_(R): 3.227′ M = 405.8 I-371 Pr

t_(R): 3.055′ M = 497.3 I-372 Pr

t_(R): 3.032′ M = 450.3 I-373 Pr

t_(R): 3.01′ M = 405.8 I-374 Pr

t_(R): 3.524′ M = 376.3 I-375 Pr

t_(R): 2.956′ M = 349.3 I-376 Pr

t_(R): 3.582′ M = 379.8 I-377 Pr

t_(R): 3.102′ M = 367.3196 I-378 Pr

t_(R): 3.066′ M = 365.8 I-379 Pr

t_(R): 3.239′ M = 345.4 I-380 Pr

t_(R): 3.445′ M = 359.4 I-381 Pr

t_(R): 3.009′ M = 391.4 I-382 Pr

t_(R): 3.223′ M = 349.3 I-383 Pr

t_(R): 3.203′ M = 399.3 I-384 Pr

t_(R): 3.205′ M = 359.4 I-385 Pr

t_(R): 3.229′ M = 391.4 I-386 Pr

t_(R): 3.257′ M = 359.4 I-387 Pr

t_(R): 3.32′ M = 391.4 I-388 Pr

t_(R): 3.145′ M = 361.4 I-389 Pr

t_(R): 3.325′ M = 395.8 I-390 Pr

t_(R): 3.221′ M = 377.4 I-391 Pr

t_(R): 3.529′ M = 407.4 I-392 Pr

t_(R): 3.471′ M = 437.5 I-393 Pr

t_(R): 3.498′ M = 455.4 I-394 Pr

t_(R): 3.828′ M = 521.5

In Table 3, further examples compounds of the general formula (I)

wherein R¹, R², R³, R⁴, R^(5a), R^(5b), R^(5c), R^(5d), A¹ and A² ineach case have the meaning given in the corresponding line and whereinA³ and A⁴ are each CH.

TABLE 3 I R¹ R² R³ R⁴ R^(5a) R^(5b) R^(5c) R^(5d) A¹ A² LC/MS I-395#-CH₂CN H Br H H CF₂ H H CH CH t_(R): 3.383′ M = 406.1 I-396 n-butyl HBr H H CHF₂ H H CH CH t_(R): 3.300′ M = 424.0 I-397 #-CH(CH₂CH₃)₂ H Br HH CF₃ H H CH CH t_(R): 3.373′ M = 438.0 I-398 cyclohexyl H Br H H CF₃ HH CH CH t_(R): 3.486′ M = 452.0 I-399 propargyl H Br H H CF₃ H H CH CHt_(R): 3.119′ M= 405.9 I-400 #-CH₂-thiophen-2-yl H Br H H CF₃ H H CH CHt_(R): 3.378′ M = 465.9 I-401 ethyl H Cl H H CF₃ F F CH CH t_(R): 4.647′M = 387.7 I-402 H H CF₃ A1-NH₂ H CF₃ H H C CH t_(R): 2.774′ M = 372.7I-403 2-fluoro-ethyl H Br H H CF₃ H H CH CH t_(R): 3.018′ M = 414.2I-404 2,2,2-t_(R)ifluoroethyl H Br H H CF₃ H H CH CH t_(R): 3.952′ M =450.2 I-405 #-CH₂C(O)OC(CH₃)₃ H Br H H CF₃ H H CH CH t_(R): 3.722′ M =482.3 I-406 propyl H Cl H F CF₃ H H CH CH t_(R): 4.848′ M = 383.8 I-407ethyl H Cl H H 1,1,2,2- H H CH CH t_(R): 3.144′ M = 399.8 tetrafluoro-ethoxy I-408 propargyl H Cl H H 1,1,2,2- H H CH CH t_(R): 3.135′ M =410.1 tetrafluoro- ethoxy I-409 propyl H Cl A1-F Cl CF₃ H H C CH t_(R):4.544′ M = 418.2 I-410 ethyl H Cl H H CF₃ CH₃ H CH CH t_(R): 3.235′ M =365.8 I-411 propyl H Cl H H CF₃ NEt H CH CH t_(R): 3.493′ M = 408.8I-412 cyclopropyl-methyl H Br H H CF₃ H H CH CH t_(R): 3.165′ M = 424.0I-413 cyclopentyl H Br H H CF₃ H H CH CH t_(R): 3.355′ M = 436.0 I-414#-CH₂CH(CH₃)₂ H Br H H CF₃ H H CH CH t_(R): 3.272′ M = 424.0 I-415#-CH(CH₃)CH₂CH₃ H Br H H CF₃ H H CH CH t_(R): 3.244′ M = 424.0 I-416#-CH(CH₃)₂ H Br H H CF₃ H H CH CH t_(R): 3.098′ M = 412.0 I-417#-CH(═NH)- H Br H H CF₃ H H CH CH t_(R): 3.384′ M = 437.0 cyclopropylI-418 #-CH(═NH)thien-2-yl H Br H H CF₃ H H CH CH t_(R:) 4.474′ M = 477.3I-419 ethyl H Cl H H CF₃ H H CH CH t_(R): 3.213′ M = 369.7 I-420 propylH Cl H Cl CF₃ H H CH CH t_(R): 4.711′ M = 400.2 I-421 #-CH₂-cyclopropylH Cl H H CF₃ OCH₃ H CH CH t_(R): 3.412′ M = 407.8 I-422 propyl H Cl H HCF₃ OCH₃ H CH CH t_(R): 3.386′ M = 395.8 I-423 propyl H Cl H H CF₃ CH₃ HCH CH t_(R): 3.445′ M = 379.8 I-424 benzyl H Br H H CF₃ H H CH CH t_(R):3.595′ M = 458.1 I-425 ethyl H Cl H H CHF₂ H H CH CH t_(R): 2.738′ M =333.8 I-426 #-CH₂-cyclohexyl H Br H H CF₃ H H CH CH t_(R): 3.635′ M =466.0 I-427 allyl H Br H H CF₃ H H CH CH t_(R): 3.070′ M = 410.0 I-428#-CH₂C(CH₃)3 H Br H H CF₃ H H CH CH t_(R): 3.410′ M = 440.0 I-429#-CH₂-2-furyl H Br H H CF₃ H H CH CH t_(R): 3.260′ M = 450.0 I-430propyl H Cl H CH₃ CF₃ H H CH CH t_(R): 4.892′ M = 379.8 I-431 propyl HCl A1-F CH₃ CF₃ H H C CH t_(R): 4.078′ M = 397.8 I-432 propyl H F H HC₃F₇ H H CH CH t_(R): 3.428′ M = 449.3 I-433 methyl methyl F H H CF₃ H HCH CH t_(R): 2.537′ M = 335.8 I-434 #-CH(CH₃)₂ cyclo- F H H CF₃ H H CHCH t_(R): 3.120′ M = 389.8 propyl I-435 H H Br H H CF₃ H H CH CH t_(R):2.759′ M = 370.0 I-436 ethyl H Cl H H OCF₃ H H CH CH t_(R): 2.966′ M =368.1 I-437 propyl H F A2-Cl Cl CF₃ H H CH C t_(R): 4.516′ M = 418.2I-438 n-pentyl H Br H H CF₃ H H CH CH t_(R): 3.474′ M = 440.0 I-439#-CH₂CH(CH₂CH₃)₂ H Br H H CF₃ H H CH CH t_(R): 3.592′ M = 452.0 I-4403,3,3-trifluoropropyl H Br H H CF₃ H H CH CH t_(R): 3.366′ M = 463.9I-441 CH(═NH)phenyl H Br H H CF₃ H H CH CH t_(R): 3.947′ M = 473.0 I-442#-CH(CH₃)CH(OCH₃)₂ H F A1-F H CF₃ H H C CH t_(R): 2.967′ M = 427.4 I-443propyl H Cl H H CF₃ NSO₂CH₃ H CH CH t_(R): 3.049′ M = 458.9 I-444 propylH Cl H H CF₃ NAc H CH CH t_(R): 2.914′ M = 422.8 I-445 ethyl ethyl F H HCF₃ H H CH CH t_(R): 2.903′ M = 363.8 I-446 2,2-difluoroethyl H Br H HCF₃ H H CH CH t_(R): 3.324′ M = 431.9 I-447 ethyl methyl Br H H CF₃ H HCH CH t_(R): 2.968′ M = 410.0 I-448 #-NH(CO)OC(CH₃)₃ H Br H H CF₃ H H CHCH t_(R): 3.694′ M = 483.0 I-449 propyl H Cl H H OCF₃ H H CH CH t_(R):3.248′ M = 382.0 I-450 CH(═NH)cyclohexyl H Br H H CF₃ H H CH CH t_(R):3.566′ M = 477.3 I-451 propyl H Cl H H CF₃ I H CH CH t_(R): 3.971′ M =491.7

II. EVALUATION OF PESTICIDAL ACTIVITY

The activity of the compounds of formula I of the present invention canbe demonstrated and evaluated by the following biological test.

B.1 Southern Armyworm (Spodoptera eridania, 2nd instar larvae)

The active compounds were formulated in cyclohexanone as a 10,0000 ppmsolution supplied in 1.3 ml ABgene® tubes. These tubes were insertedinto an automated electrostatic sprayer equipped with an atomizingnozzle and they served as stock solutions for which lower dilutions weremade in 50% acetone: 50% water (v/v). A nonionic surfactant (Kinetic®)was included in the solution at a volume of 0.01% (v/v). Lima beanplants (variety Sieva) were grown 2 plants to a pot and selected fortreatment at the 1^(st) true leaf stage. Test solutions were sprayedonto the foliage by an automated electrostatic plant sprayer equippedwith an atomizing spray nozzle. The plants were dried in the sprayerfume hood and then removed from the sprayer. Each pot was placed intoperforated plastic bags with a zip closure. Ten to 11 armyworm larvaewere placed into the bag and the bags zipped closed. Test plants weremaintained in a growth room at at 25° C. and 20-40% relative humidityfor 4 days, avoiding direct exposure to fluorescent light (24 hourphotoperiod) to prevent trapping of heat inside the bags. Mortality andreduced feeding were assessed 4 days after treatment, compared tountreated control plants.

In this test, compounds I-1, I-2, I-3, I-4, I-5, I-8, I-10, I-11, I-13,I-16, I-17, I-21, I-23, I-28, I-29, I-30, I-31, I-37, I-38, I-40, I-41,I-46, I-47, I-49, I-53, I-54, I-56, I-57, I-58, I-60, I-61, I-63, I-64,I-67, I-71, I-72, I-73, I-74, I-75, I-77, I-78, I-79, I-80, I-82, I-83,I-84, a85, I-88, I-91, I-94, I-99, I-100, I-101, I-102, I-109, I-110,I-111, I-114, I-117, I-118, I-119, -a120, I-123, I-124, I-125, I-128,I-130, I-132, I-133, I-136, I-143, I-151, I-152, I-153, I-154, I-155,I-157, I-159, I-160, I-161, I-162, I-163, I-167, I-168, I-169, I-170,I-172, I-175, I-176, I-177, I-182, I-183, I-184, I-185, I-186, I-187,I-191, I-192, I-193, I-194, I-195, I-196, I-197, I-198, I-200, I-201,I-202, I-204, I-205, I-206, I-207, I-208, I-210, I-218, I-219, I-222,I-223, I-224, I-225, I-226, I-227, I-229, I-230, I-231, I-233, I-234,I-235, I-236, I-244, I-245, I-246, I-248, I-249, I-250, I-251, I-252,I-253, I-254, I-264, I-266, I-268, I-269, I-270, I-273, I-292, I-295,I-297, I-299, I-300, I-301, I-302, I-303, I-304, I-305, I-306, I-307,I-308, I-309, I-310, I-311, I-312, I-323, I-327, I-329, I-330, I-331,I-332, I-335, I-395, I-396, I-397, I-399, I-400, I-403, I-406, I-407,I-408, I-412, I-413, I-414, I-415, I-416, I-417, I-420, I-421, I-424,I-430, I-431, I-433, I-438, I-440, I-445, I-446, I-447 and I-451 at 300ppm showed a mortality of at least 50% in comparison with untreatedcontrols.

B.2 Silverleaf Whitefly (Bemisia argentifolii, adult)

The active compounds were formulated in cyclohexanone as a 10,0000 ppmsolution supplied in 1.3 ml ABgene® tubes. These tubes were insertedinto an automated electrostatic sprayer equipped with an atomizingnozzle and they served as stock solutions for which lower dilutions weremade in 50% acetone: 50% water (v/v). A nonionic surfactant (Kinetic®)was included in the solution at a volume of 0.01% (v/v). Cotton plantsat the cotyledon stage (one plant per pot) were sprayed by an automatedelectrostatic plant sprayer equipped with an atomizing spray nozzle. Theplants were dried in the sprayer fume hood and then removed from thesprayer. Each pot was placed into a plastic cup and 10 to 12 whiteflyadults (approximately 3-5 days old) were introduced. The insects werecollected using an aspirator and 0.6 cm, nontoxic Tygon® tubing (R-3603)connected to a barrier pipette tip. The tip, containing the collectedinsects, was then gently inserted into the soil containing the treatedplant, allowing insects to crawl out of the tip to reach the foliage forfeeding. Cups were covered with a reusable screened lid (150-micron meshpolyester screen PeCap from Tetko, Inc.). Test plants were maintained ina growth room at 25° C. and 20-40% relative humidity for 3 days,avoiding direct exposure to fluorescent light (24 hour photoperiod) toprevent trapping of heat inside the cup. Mortality was assessed 3 daysafter treatment, compared to untreated control plants.

In this test, compounds I-11, I-78, I-120, I-121, I-182, I-195, I-196,I-244, I-413 and I-442 at a test concentration of 500 ppm showed amortality of at least 50% in comparison with untreated controls.

B.3 Colorado potato beetle (Leptinotarsa decemlineata, adult)

The active compounds were formulated in cyclohexanone as a 10,0000 ppmsolution supplied in 1.3 ml ABgene® tubes. These tubes were insertedinto an automated electrostatic sprayer equipped with an atomizingnozzle and they served as stock solutions for which lower dilutions weremade in 50% acetone:50% water (v/v). A nonionic surfactant (Kinetic®)was included in the solution at a volume of 0.01% (v/v). Eggplants weregrown 2 plants to a pot and were selected for treatment at the 1^(st)true leaf stage. Test solutions were sprayed onto the foliage by anautomated electrostatic plant sprayer equipped with an atomizing spraynozzle. The plants were dried in the sprayer fume hood and then removedfrom the sprayer. The treated foliage was then cut and removed from thepot and placed in a 5-inch Petri dish lined with moistened filter paper.Five beetle larvae were introduced into each Petri dish and the dish wascovered by a Petri dish lid. Petri dishes were maintained in a growthroom at 25° C. and 20-40% relative humidity for 4 days, avoiding directexposure to fluorescent light (24 hour photoperiod) to prevent trappingof heat inside the dishes. Mortality and reduced feeding were assessed 4days after treatment, compared to untreated control plants.

In this test, compound I-201 at a test concentration of 300 ppm showed amortality of at least 50% in comparison with untreated controls.

B.4 Diamondback moth (Plutella xylostella)

The active compound was dissolved at the desired concentration in amixture of 1:1 (vol:vol) distilled water:acetone. The test solution wasprepared at the day of use.

The activity against Plutella xylostella can be tested by the followingexperiments:

Leaves of Chinese cabbage were dipped in test solution and air-dried.Treated leaves were placed in petri dished lined with moist filterpaper. Mortality was recorded 24, 72, and 120 hours after treatment.

In this test, compounds I-1, I-4, I-5, I-8, I-10, I-11, I-13, I-16,I-17, I-23, I-28, I-29, I-33, I-36, I-37, I-38, I-46, I-47, I-48, I-51,I-52, I-54, I-56, I-57, I-58, I-60, I-61, I-63, I-71, I-73, I-74, I-75,I-76, I-77, I-78, I-79, I-82, I-83, I-84, I-85, I-88, I-94, I-99, I-100,I-101, I-102, I-103, I-105, I-109, I-110, I-111, I-114, I-117, I-118,I-120, I-121, I-124, I-125, I-131, I-133, I-135, I-136, I-142, I-143,I-151, I-152, I-153, I-154, I-157, I-159, I-160, I-162, I-163, I-169,I-170, I-176, I-177, I-185, I-186, I-187, I-191, I-193, I-194, I-195,I-196, I-198, I-201, I-202, I-204, I-205, I-206, I-207, I-209, I-210,I-211, I-212, I-213, I-215, I-218, I-219, I-21, I-223, I-224, I-225,I-227, I-228, I-229, I-230, I-231, I-233, I-234, I-235, I-236, I-238,I-241, I-61, I-264, I-266, I-267, I-268, I-270, I-272, I-285, I-292,I-296, I-297, I-299, I-300, I-301, I-302, I-303, I-304, I-306, I-307,I-313, I-395, I-396, I-397, I-399, I-403 and I-404 at a testconcentration of 500 ppm showed a mortality of at least 50% incomparison with untreated controls.

B.5 Orchid thrips (Dichromothrips corbetti)

Dichromothrips corbetti adults used for bioassay were obtained from acolony maintained continuously under laboratory conditions. For testingpurposes, the test compound was diluted to a concentration of 300 ppm(wt compound: vol diluent) in a 1:1 mixture of acetone:water (vol:vol),plus 0.01% vol/vol Kinetic® surfactant. Thrips potency of each compoundwas evaluated by using a floral-immersion technique. Plastic petridishes were used as test arenas. All petals of individual, intact or-chid flowers were dipped into treatment solution and allowed to dry.Treated flowers were placed into individual petri dishes along with10-15 adult thrips. The petri dishes were then covered with lids. Alltest arenas were held under continuous light and a temperature of about28° C. for duration of the assay. After 4 days, the numbers of livethrips were counted on each flower, and along inner walls of each petridish. The level of thrips mortality was extrapolated from pre-treatmentthrips numbers.

In this test, compounds I-5, I-8, I-29, I-56, I-71, I-100, I-101, I-111,I-124, I-131, I-133, I-162, I-169, I-170, I-201, I-202, I-225, I-227,I-231, I-235, I-242, I-243, I-412, I-434 and I-445 at a testconcentration of 500 ppm showed a mortality of at least 50% incomparison with untreated controls.

B.6 Vetch aphid (Megoura viciae)

For evaluating control of vetch aphid (Megoura viciae) through contactor systemic means the test unit consists of 24-well-microtiter platescontaining broad bean leaf disks. The compounds were formulated using asolution containing 75% v/v water and 25% v/v DMSO. Differentconcentrations of formulated compounds were sprayed onto the leaf disksat 2.5 μl, using a custom built micro atomizer, at two replications.After application, the leaf disks were air-dried and 5-8 adult aphidsplaced on the leaf disks inside the microtiter plate wells. The aphidswere then allowed to suck on the treated leaf disks and incubated atabout 23±1° C. and about 50±5% relative humidity for 5 days. Aphidmortality and fecundity was then visually assessed.

In this test, compounds I-11, I-32, I-34, I-35, I-47, I-66, I-78, I-84,I-86, I-87, I-122, I-162, I-164, I-165, I-169, I-170, I-197, I-205,I-217, I-220, I-232, I-233, I-235, I-240, I-241, I-264, I-282, I-330,I-413, I-415, I-418 and I-425 at a test concentration of 800 ppm showeda mortality of at least 50%.

B.7 Green Peach Aphid (Myzus persicae, mixed life stages)

The active compounds were formulated in cyclohexanone as a 10,000 ppmsolution supplied in tubes. The tubes were inserted into an automatedelectrostatic sprayer equipped with an atomizing nozzle and they servedas stock solutions for which lower dilutions were made in 50%acetone:50% water (v/v). A nonionic surfactant (Kinetic®) was includedin the solution at a volume of 0.01% (v/v).

Bell pepper plants at the first true-leaf stage were infested prior totreatment by placing heavily infested leaves from the main colony on topof the treatment plants. Aphids were allowed to transfer overnight toaccomplish an infestation of 30-50 aphids per plant and the host leaveswere removed. The infested plants were then sprayed by an automatedelectrostatic plant sprayer equipped with an atomizing spray nozzle. Theplants were dried in the sprayer fume hood, removed, and then maintainedin a growth room under fluorescent lighting in a 24-hr photoperiod atabout 25° C. and about 20-40% relative humidity. Aphid mortality on thetreated plants, relative to mortality on untreated control plants, wasdetermined after 5 days.

In this test, compounds I-29, I-32, I-33, I-35, I-57, I-60, I-77, I-100,I-101, I-102, I-105, I-109, I-114, I-118, I-119, I-120, I-150, I-162,I-165, I-169, I-191, I-195, I-217, I-218, I-221, I-223, I-225, I-227,I-228, I-235, I-239, I-240, I-241, I-270, I-271, I-272, I-273, I-274,I-279, I-280, I-283, I-284, I-286, I-288, I-289, I-290, I-291, I-292,I-296, I-332, I-335, I-402, I-415, I-418, I-425, I-436 and I-448 at atest concentration of 800 ppm showed a mortality of at least 50%.

B.8 Boll weevil (Anthonomus grandis)

For evaluating control of boll weevil (Anthonomus grandis) the test unitconsists of 24-well-microtiter plates containing an insect diet and20-30 A. grandis eggs. The compounds were formulated using a solutioncontaining 75% v/v water and 25% v/v DMSO. Different concentrations offormulated compounds were sprayed onto the insect diet at 20 μl, using acustom built micro atomizer, at two replications. After application,microtiter plates were incubated at about 23±1° C. and about 50±5%relative humidity for 5 days. Egg and larval mortality was then visuallyassessed.

In this test, compounds I-10, I-11, I-13, I-17, I-28, I-29, I-31, I-34,I-37, I-38, I-40, I-41, I-46, I-58, I-60, I-61, I-64, I-71, I-73, I-77,I-78, I-79, I-80, I-82, I-83, I-100, I-101, I-102, I-108, I-109, I-111,I-113, I-114, I-116, I-119, I-120, I-121, I-124, I-132, I-133, I-152,I-153, I-154, I-157, I-159, I-162, I-163, I-169, I-182, I-191, I-193,I-194, I-195, I-199, I-201, I-202, I-205, I-207, I-208, I-211, I-218,I-219, I-221, I-222, I-223, I-25, I-227, I-229, I-230, I-231, I-232,I-233, I-234, I-235, I-236, I-240, I-243, I-255, I-261, I-264, I-267,I-269, I-271, I-272, I-273, I-277, I-280, I-281, I-282, I-283, I-284,I-285, I-289, I-290, I-291, I-92, I-295, I-330, I-335, I-336, I-395,I-396, I-397, I-399, I-403, I-406, I-412, I-415, I-416, I-420, I-24,I-425, I-427, I-428, I-430, I-431, I-435, I-438 and I-449 at a testconcentration of 800 ppm showed a mortality of at least 50%.

B. 9 Mediterranean fruitfly (Ceratitis capitata)

For evaluating control of Mediterranean fruitfly (Ceratitis capitata)the test unit consisted of microtiter plates containing an insect dietand 50-80 C. capitata eggs. The compounds were formulated using asolution containing 75% v/v water and 25% v/v DMSO. Differentconcentrations of formulated compounds were sprayed onto the insect dietat 5 μl, using a custom built micro atomizer, at two replications. Afterapplication, microtiter plates were incubated at about 28±1° C. andabout 80±5% relative humidity for 5 days. Egg and larval mortality wasthen visually assessed.

In this test, compounds I-10, I-11, I-12, I-13, I-14, I-16, I-17, I-19,I-28, I-29, I-34, I-37, I-38, I-45, I-46, I-47, I-49, I-56, I-57, I-61,I-64, I-71, I-72, I-73, I-74, I-75, I-77, I-78, I-79, I-80, I-81, I-82,I-83, I-87, I-98, I-99, I-100, I-101, I-102, I-105, I-107, I-109, I-111,I-114, I-115, I-117, I-118, I-119, I-120, I-121, I-125, I-133, I-151,I-152, I-153, I-154, I-155, I-157, I-159, I-162, I-163, I-169, I-182,I-191, I-193, I-195, I-196, I-199, I-201, I-202, I-205, I-206, I-207,I-208, I-209, I-210, I-213, I-215, I-218, I-219, I-221, I-222, I-223,I-224, I-225, I-226, I-227, I-228, I-229, I-230, I-231, I-233, I-234,I-235, I-236, I-237, I-239, I-241, I-255, I-257, I-264, I-267, I-269,I-270, I-272, I-276, I-295, I-330, I-331, I-332, I-335, I-395, I-396,I-397, I-399, I-400, I-403, I-404, I-406, I-407, I-408, I-409, I-412,I-414, I-415, I-416, I-417, I-418, I-420, I-424, I-427, I-431, I-434,I-437, I-438, I-440, I-441, I-445, I-446, I-447, I-448 and I-449 at atest concentration of 800 ppm showed a mortality of at least 50%.

B.10 Tobacco budworm (Heliothis virescens)

For evaluating control of tobacco budworm (Heliothis virescens) the testunit consists of 96-well-microtiter plates containing an insect diet and15-25 H. virescens eggs. The compounds were formulated using a solutioncontaining 75% v/v water and 25% v/v DMSO. Different concentrations offormulated compounds were sprayed onto the insect diet at 10 μl, using acustom built micro atomizer, at two replications. After application,microtiter plates were incubated at about 28±1° C. and about 80±5%relative humidity for 5 days. Egg and larval mortality was then visuallyassessed.

In this test, compounds I-8, I-10, I-11, I-12, I-13, I-16, I-17, I-19,I-28, I-29, I-32, I-34, I-37, I-38, I-39, I-40, I-41, I-46, I-47, I-49,I-56, I-57, I-60, I-61, I-63, I-64, I-71, I-72, I-73, I-74, I-75, I-76,I-77, I-78, I-79, I-80, I-82, I-83, I-84, I-85, I-99, I-100, I-101,I-102, I-109, I-111, I-114, I-115, I-116, I-117, I-118, I-119, I-120,I-121, I-122, I-124, I-125, I-126, I-130, I-132, I-133, I-151, I-152,I-153, I-154, I-157, I-158, I-159, I-160, I-161, I-162, I-163, I-168,I-169, I-182, I-191, I-193, I-194, I-195, I-196, I-197, I-199, I-200,I-201, I-202, I-204, I-205, I-206, I-207, I-208, I-209, I-210, I-212,I-215, I-216, I-218, I-219, I-221, I-222, I-223, I-224, I-225, I-226,I-227, I-228, I-229, I-230, I-231, I-232, I-233, I-234, I-235, I-236,I-237, I-238, I-239, I-241, I-255, I-256, I-257, I-261, I-264, I-266,I-267, I-269, I-270, I-271, I-272, I-273, I-280, I-282, I-283, I-284,I-287, I-290, I-291, I-292, I-295, I-329, I-330, I-331, I-332, I-335,I-395, I-396, I-397, I-399, I-400, I-403, I-404, I-405, I-406, I-407,I-408, I-409, I-412, I-413, I-414, I-415, I-416, I-420, I-424, I-425,I-427, I-430, I-431, I-433, I-435, I-436, I-437, I-438, I-439, I-440,I-445, I-446, I-447, I-448, I-449 at a test concentration of 800 ppmshowed a mortality of at least 50%.

1-18. (canceled)
 19. A method for controlling or combating invertebratepests attack or infestation which method comprises treating the pests,their food supply, their habitat, their breeding ground, the plant, theplant propagation material, soil, area, material or environment in whichthe pests are growing or may grow, with a pesticidally effective amountof a compound of the formula (I)

wherein A¹, A², A³ and A⁴ are N, NX or CR⁴ wherein X is a lone pair orO, with the proviso that at most three of A¹, A², A³ and A⁴ are N or NX;R¹, R² are selected independently from one another from the groupconsisting of hydrogen, CN, NO₂, C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl,C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, wherein the carbon atoms of theaforementioned aliphatic and cycloaliphatic radicals may beunsubstituted or substituted with one or more R⁶; Si(R¹¹)₂R¹², OR⁷,S(O)_(m)R⁷, NR⁸R⁹, N═C(R⁶)₂, C(═O)R⁶, C(═S)R⁶, C(═NR⁸)R⁶ and a 3-, 4-,5-, 6- or 7-membered heterocyclic ring, wherein said heterocyclic ringis saturated or partially saturated, comprises 1, 2 or 3 heteroatomsselected from the group consisting of oxygen, nitrogen and sulfur,wherein the nitrogen and/or the sulfur atom(s) may be oxidized, isunsubstituted or substituted with one to five R¹⁰, and wherein one ortwo CH₂ groups in said heterocyclic ring may be replaced by one or twoC═O groups; R³ is selected from the group consisting of hydrogen,halogen, cyano, azido, nitro, SCN, SF₅, C₃-C₈-cycloalkyl,C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, wherein the carbon atoms of theaforementioned aliphatic and cycloaliphatic radicals may beunsubstituted or substituted with one or more R⁶; Si(R¹¹)₂R¹², OR⁷,S(O)_(m)R⁷, N(R⁸)R⁹, N═C(R⁶)₂, C(═O)R⁶, C(═S)R⁶, C(═NR⁸)R⁶, phenyl whichmay be substituted with 1, 2, 3, 4 or 5 radicals R¹⁰; and a 3-, 4-, 5-,6- or 7-membered heterocyclic ring, wherein said heterocyclic ring issaturated or partially saturated, comprises 1, 2 or 3 heteroatoms orheteroatom groups selected from the group consisting of N, O, S, NO, SOand SO₂, is unsubstituted or substituted with one to five radicals R¹⁰,and wherein one or two CH₂ groups in said heterocyclic ring may bereplaced by one or two C═O groups; each R⁴ is selected independentlyfrom the group consisting of hydrogen, halogen, cyano, azido, nitro,SCN, SF₅, C₃-C₈-cycloalkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, wherein thecarbon atoms of the aforementioned aliphatic and cycloaliphatic radicalsmay be unsubstituted or substituted with one or more R⁶; Si(R¹¹)₂R¹²,OR⁷, S(O)_(m)R⁷, N(R⁸)R⁹, N═C(R⁶)₂, C(═O)R⁶, C(═S)R⁶, C(═NR⁸)^(R6),C(═O)N(R⁸)R⁹, C(═S)N(R⁸)R⁹, phenyl which may be substituted with 1, 2,3, 4 or 5 radicals R¹⁰; and a 3-, 4-, 5-, 6- or 7-membered heterocyclicring, wherein said heterocyclic ring is saturated or partiallyunsaturated or aromatic, comprises 1, 2 or 3 heteroatoms or heteroatomgroups selected from the group consisting of N, O, S, NO, SO and SO₂, isunsubstituted or substituted with one to five radicals R¹⁰, and whereinone or two CH₂ groups in said saturated or partially saturated rings maybe replaced by one or two C═O groups; or two radicals R⁴ bound onadjacent carbon atoms together form a group selected from the groupconsisting of —CH₂CH₂CH₂CH₂—, —CH═CH—CH═CH—, —N═CH—CH═CH—, —CH═N—CH═CH—,—N═CH—N═CH—, —OCH₂CH₂CH₂—, —OCH═CHCH₂—, —CH₂OCH₂CH₂—, —OCH₂CH₂O—,—OCH₂OCH₂—, —CH₂CH₂CH₂—, —CH═CHCH₂—, —CH₂CH₂O—, —CH═CHO—, —CH₂OCH₂—,—CH₂C(═O)O—, —C(═O)OCH₂—, —O(CH₂)O—, —SCH₂CH₂CH₂—, —SCH═CHCH₂—,—CH₂SCH₂CH₂—, —SCH₂CH₂S—, —SCH₂SCH₂—, —CH₂CH₂S—, —CH═CHS—, —CH₂SCH₂—,—CH₂C(═S)S—, —C(═S)SCH₂—, —S(CH₂)S—, —CH₂CH₂NR⁸—, —CH₂CH═N—,—CH═CH—NR⁸—, —OCH═N— and —SCH═N—, wherein in each of the above group,one to five hydrogen atoms independently of each other may be replacedby one to five substituents selected from the group consisting ofhalogen, methyl, halomethyl, hydroxyl, methoxy and halomethoxy, or oneor two CH₂ groups of the above groups may be replaced by one or two C═Ogroups; R^(5a) is selected from the group consisting of hydrogen,halogen, cyano, azido, nitro, SCN, SF₅, C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl,C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, wherein the carbon atoms of theaforementioned aliphatic and cycloaliphatic radicals may beunsubstituted or substituted with one or more R⁶; Si(R¹¹)₂R¹², OR⁷,S(O)_(m)R⁷, N(R⁸)R⁹, N═C(R⁶)₂, C(═O)R⁶, C(═S)R⁶, C(═NR⁸)R⁶, phenyl whichmay be substituted with 1, 2, 3, 4 or 5 radicals R¹⁰; and a 3-, 4-, 5-,6- or 7-membered heterocyclic ring, wherein said heterocyclic ring issaturated or partially unsaturated or aromatic, comprises 1, 2 or 3heteroatoms or heteroatom groups selected from the group consisting ofN, O, S, NO, SO and SO₂, is unsubstituted or substituted with one tofive radicals R¹⁰, and wherein one or two CH₂ groups in said saturatedor partially saturated rings may be replaced by one or two C═O groups;or R^(5a) may form together with the adjacent carbon atom R^(5b) a 5- or6-membered ring which is at least substituted with one halogen; R^(5b)is selected from the group consisting of C₁-C₆-alkyl, C₃-C₆-cycloalkyl,C₁-C₆-alkoxy and C₁-C₆-cycloalkoxy, wherein each mentioned radical issubstituted with at least one halogen, may be further partially or fullyhalogenated, and may be substituted with one to five radicals R⁶; orR^(5b) may form together with the adjacent carbon atom R^(5c) or R^(5a)a 5- or 6-membered ring which is substituted with at least one halogen;R^(5c) is selected from the group consisting of hydrogen, halogen,cyano, azido, nitro, SCN, SF₅, C₃-C₈-cycloalkyl, C₂-C₁₀-alkenyl,C₂-C₁₀-alkynyl, wherein the carbon atoms of the aforementioned aliphaticand cycloaliphatic radicals may be unsubstituted or substituted with oneor more R⁶; Si(R¹¹)₂R¹², OR⁷, S(O)_(m)R⁷, N(R⁸)R⁹, N═C(R⁶)₂, C(═O)OR⁷,C(═S)OR⁷, C(═NR⁸)R⁶, C(═O)N(R⁸)R⁹, C(═S)N(R⁸)R⁹, phenyl which may besubstituted with 1, 2, 3, 4 or 5 radicals R¹⁰; and a 3-, 4-, 5-, 6- or7-membered heterocyclic ring, wherein said heterocyclic ring issaturated, partially unsaturated or aromatic, comprises 1, 2 or 3heteroatoms or heteroatom groups selected from the group consisting ofN, O, S, NO, SO and SO₂, is unsubstituted or substituted with one tofive radicals R¹⁰, and wherein one or two CH₂ groups in said saturatedor partially saturated rings may be replaced by one or two C═O groups;or R^(5c) may form together with the adjacent carbon atom R^(5b) orR^(5d) a 5- or 6-membered ring which is substituted with at least onehalogen in case of R^(5b) being involved; R^(5d) is selected from thegroup consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF₅,C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, whereinthe carbon atoms of the aforementioned aliphatic and cycloaliphaticradicals may be unsubstituted or substituted with one or more R⁶;Si(R¹¹)₂R¹², OR⁷, S(O)_(m)R⁷, S(O)_(m)N(R⁸)R⁹, N(R⁸)R⁹, N═C(R⁶)₂,C(═O)R⁶, C(═S)R⁶, C(═NR⁸)R⁶, phenyl which may be substituted with 1, 2,3, 4 or 5 radicals R¹⁰; and a 3-, 4-, 5-, 6- or 7-membered heterocyclicring, wherein said heterocyclic ring is saturated, partially unsaturatedor aromatic, comprises 1, 2 or 3 heteroatoms or heteroatom groupsselected from the group consisting of N, O, S, NO, SO and SO₂, isunsubstituted or substituted with one to five radicals R¹⁰, and whereinone or two CH₂ groups in said saturated or partially saturated rings maybe replaced by one or two C═O groups; or R^(5d) may form together withthe adjacent carbon atom R^(5c) or with R¹ or R² a 5- or 6-memberedring; R⁶ is selected independently from the group consisting ofhydrogen, halogen, cyano, azido, nitro, SCN, SF₅, C₁-C₆-alkyl,C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl,C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, wherein the carbon atom of the aforementioned aliphaticand cycloaliphatic radicals may be substituted with one or more R^(c);Si(R¹¹)₂R¹², OR^(o), O(CO)R^(c), O(CS)R^(c), S(O)_(m)R^(o),S(O)_(m)N(R^(n))₂, S(CO)R^(c), S(CS)R^(c), S(C═NR^(n))R^(c), N(R^(n))₂,N(R^(n))C(═O)R^(c), N(R^(n))C(═S)R^(c), NS(O)_(m)R^(o), N═C(R^(c))₂,C(═O)R^(c), C(═S)R^(c), C(═NR^(n))R^(c), C(═O)N(R^(n))₂, C(═S)N(R)₂,phenyl which may be substituted with 1, 2, 3, 4 or 5 radicals R¹⁰; and a3-, 4-, 5-, 6- or 7-membered heterocyclic ring, wherein saidheterocyclic ring is saturated, partially unsaturated or aromatic,comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from thegroup consisting of N, O, S, NO, SO and SO₂, is unsubstituted orsubstituted with one to five radicals R¹⁰, and wherein one or two CH₂groups in said saturated or partially saturated rings may be replaced byone or two C═O groups; or two vicinally bound radicals R⁶ together forma group selected from ═C(R^(c))₂, ═S(O)_(m)R^(o), ═S(O)_(m)N(R^(n))₂,═NR^(n) and ═NN(R^(n))₂; R⁷ is selected independently from the groupconsisting of hydrogen, cyano, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl,C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, wherein the carbon atom of the aforementioned aliphaticand cycloaliphatic radicals may be substituted with one or more R^(c);Si(R¹¹)₂R¹², OR^(o), O(CO)R^(c), O(CS)R^(c), S(O)_(m)R^(o),S(O)_(m)N(R^(n))₂, S(CO)R^(c), S(CS)R^(c), S(C═NR^(n))R^(c), N(R^(n))₂,N(R^(n))C(═O)R^(c), N(R^(n)C(═S)R^(c), NS(O)_(m)R^(o), N═C(R^(c))₂,C(═O)R^(c), C(═S)R^(c), C(═NR^(n))R^(c), C(═O)N(R^(n))₂, C(═S)N(R^(n))₂,phenyl which may be substituted with 1, 2, 3, 4 or 5 radicals R¹⁰; and a3-, 4-, 5-, 6- or 7-membered heterocyclic ring, wherein saidheterocyclic ring is saturated, partially unsaturated or aromatic,comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from thegroup consisting of N, O, S, NO, SO and SO₂, is unsubstituted orsubstituted with one to five radicals R¹⁰, and wherein one or two CH₂groups in said saturated or partially saturated rings may be replaced byone or two C═O groups; with the proviso that R⁷ is not C₁-C₆-alkoxy orC₁-C₆-haloalkoxy if it is bound to an oxygen atom; R⁸, R⁹ are selectedindependently from one another and independently of each occurrence fromthe group consisting of hydrogen, CN, NO₂, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl,C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, wherein the carbon atom of the aforementioned aliphaticand cycloaliphatic radicals may be substituted with one or more R^(c);Si(R¹¹)₂R¹², OR^(o), O(CO)R^(c), O(CS)R^(c), S(O)_(m)R^(o),S(O)_(m)N(R^(n))₂, S(CO)R^(c), S(CS)R^(c), S(C═NR^(n))R^(c), N(R^(n))₂,N(R^(n))C(═O)R^(c), N(R^(n))C(═S)R^(c), NS(O)_(m)R^(o), N═C(R^(c))₂,C(═O)R^(c), C(═S)R^(c), C(═NR^(n))R^(c), C(═O)N(R^(n))₂, C(═S)N(R^(n))₂phenyl which may be substituted with 1, 2, 3, 4 or 5 radicals R¹⁰; and a3-, 4-, 5-, 6- or 7-membered heterocyclic ring, wherein saidheterocyclic ring is saturated, partially unsaturated or aromatic,comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from thegroup consisting of N, O, S, NO, SO and SO₂, is unsubstituted orsubstituted with one to five radicals R¹⁰, and wherein one or two CH₂groups in said saturated or partially saturated rings may be replaced byone or two C═O groups; R¹⁰ is selected independently from the groupconsisting of halogen, cyano, azido, nitro, SCN, SF₅, C₁-C₆-alkyl,C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl,C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, wherein the carbon atom of the aforementioned aliphaticand cycloaliphatic radicals may be substituted with one or more R^(c);Si(R¹¹)₂R¹², OR^(o), O(CO)R^(c), O(CS)R^(c), S(O)_(m)R^(o),S(O)_(m)N(R^(n))₂, S(CO)R^(c), S(CS)R^(c), S(C═NR^(n))R^(c), N(R^(n))₂,N(R^(n))C(═O)R^(c), N(R^(n))C(═S)R^(c), NS(O)_(m)R^(o), N═C(R^(c))₂,C(═O)R^(c), C(═S)R^(c), C(═NR^(n))R^(c), C(═O)N(R^(n))₂, C(═S)N(R^(n))₂,phenyl which may be substituted with one to five radicals selectedindependently from halogen, cyano, nitro, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₆-alkoxy and C₁-C₆-haloalkoxy; and a 3-, 4-, 5-, 6- or 7-memberedheterocyclic ring, wherein said heterocyclic ring is saturated orunsaturated, comprises 1, 2 or 3 heteroatoms or heteroatom groupsselected from the group consisting of N, O, S, NO, SO and SO₂, isunsubstituted or substituted with one to five radicals selectedindependently from the group consisting of halogen, cyano, nitro,C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy; or tworadicals R¹⁰ bound on adjacent atoms together form a group selected from—CH₂CH₂CH₂CH₂—, —CH═CH—CH═CH—, —N═CH—CH═CH—, —CH═N—CH═CH—, —N═CH—N═CH—,—OCH₂CH₂CH₂—, —OCH═CHCH₂—, —CH₂OCH₂CH₂—, —OCH₂CH₂O—, —OCH₂OCH₂—,—CH₂CH₂CH₂—, —CH═CHCH₂—, —CH₂CH₂O—, —CH═CHO—, —CH₂OCH₂—, —CH₂C(═O)O—,—C(═O)OCH₂—, —O(CH₂)O—, —SCH₂CH₂CH₂—, —SCH═CHCH₂—, —CH₂SCH₂CH₂—,—SCH₂CH₂S—, —SCH₂SCH₂—, —CH₂CH₂S—, —CH═CHS—, —CH₂SCH₂—, —CH₂C(═S)S—,—C(═S)SCH₂—, —S(CH₂)S—, —CH₂CH₂NR⁸—, —CH₂CH═N—, —CH═CH—NR⁸—, —OCH═N— and—SCH═N—, wherein in each of the above groups, one to five hydrogen atomsindependently of each other may be replaced by one to five substituentsselected from the group consisting of halogen, methyl, halomethyl,hydroxyl, methoxy and halomethoxy, or one or two or more CH₂ groups ofthe above groups may be replaced by one or two C═O groups; R¹¹, R¹² areselected independently of each other and independently of eachoccurrence from the group consisting of C₁-C₄-alkyl, C₃-C₆-cycloalkyl,C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl and benzyl; R^(c) is selectedindependently from the group consisting of hydrogen, halogen, cyano,azido, nitro, SCN, SF₅, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,C₁-C₆-haloalkylsulfonyl, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl,C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,C₂-C₆-haloalkynyl, phenyl, and a 3-, 4-, 5-, 6- or 7-memberedheterocyclic ring, wherein said heterocyclic ring is saturated,partially unsaturated or aromatic, comprises 1, 2 or 3 heteroatoms orheteroatom groups selected from CO, N, O, S, NO, SO and SO₂, isunsubstituted or substituted with one to five radicals, which areselected independently of each other from halogen, cyano, nitro,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; R^(o)is selected independently from the group consisting of hydrogen, cyano,C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl,C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl,C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl, C₃-C₈-halocycloalkyl,C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl,phenyl, and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring, whereinsaid heterocyclic ring is saturated, partially unsaturated or aromatic,comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from CO,N, O, S, NO, SO and SO₂, is unsubstituted or substituted with one tofive radicals, which are selected independently of each other fromhalogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy andC₁-C₄-haloalkoxy; with the proviso that R^(o) is not C₁-C₆-alkoxy orC₁-C₆-haloalkoxy if it is bound to an oxygen atom; R^(n) is selectedindependently from the group consisting of hydrogen, CN, NO₂,C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl,C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl,C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl, C₃-C₈-halocycloalkyl,C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl,phenyl, and a 3-, 4-, 5-, 6- or 7-membered saturated heterocyclic ring,wherein said heterocyclic ring is saturated, partially unsaturated oraromatic, comprises 1, 2 or 3 heteroatoms or heteroatom groups selectedfrom CO, N, O, S, NO, SO and SO₂, is unsubstituted or substituted withone to five radicals, which are selected independently of each otherfrom halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxyand C₁-C₄-haloalkoxy; m is independently 0, 1 or 2; p is 0, 1, 2, 3 or4; or enantiomers or diastereoisomers thereof or their agriculturally orveterinarily acceptable salts, or a composition comprising at least onecompound of formula I.
 20. The method according to claim 19, whereinR^(5b) is selected from the group consisting of C₁-C₆-alkyl,C₃-C₆-cycloalkyl, C₁-C₆-alkoxy and C₁-C₆-cycloalkoxy, wherein eachmentioned radical is at least substituted with one halogen.
 21. Themethod according to claim 19, wherein R³ is selected from the groupconsisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF₅,C₁-C₆-haloalkyl, C₃-C₆-halocycloalkyl, C₁-C₆-haloalkoxy,C₃-C₆-halocycloalkoxy, Si(R¹¹)₂R¹², OR⁷, S(O)_(m)R⁷, N(R⁸)R⁹, N═(R⁶)₂,C(═O)R⁶, C(═S)R⁶ and C(═NR⁸)R⁶.
 22. The method according to claim 19,wherein R^(5b) is selected from the group consisting of C₁-C₆-haloalkyland C₁-C₆-haloalkoxy; R³ is selected from the group consisting ofhydrogen, halogen, CN, NO₂, C(═NR⁸)R⁶, C₁-C₆-haloalkyl,C₃-C₆-halocycloalkyl, C₁-C₆-haloalkoxy and C₃-C₆-halocycloalkoxy. 23.The method according to claim 19, wherein R^(5b) is CF₃; R³ is halogen;A¹, A², A³ and A⁴ are CR⁴; R^(5c) and R^(5d) are independently from oneanother hydrogen, halogen, C₁-C₆-alkyl or C₁-C₆-haloalkyl; R^(5a) andeach R⁴ are independently from one another hydrogen, halogen, CN, NO₂,C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy or C₁-C₆-cycloalkoxy. 24.The method according to claim 19, wherein R^(5b) is CF₃; R³ is halogen;A¹, A², A³ and A⁴ are CR⁴; R^(5c) and R^(5d) are hydrogen; R^(5a) andeach R⁴ are independently from one another hydrogen, halogen,C₁-C₆-alkyl, or C₁-C₆-haloalkyl.
 25. A method for protecting plants orplant propagation materials from attack or infestation by invertebratepests, which method comprises treating the plants or the plantpropagation materials or the materials, surfaces or spaces in which theygrow with a pesticidally effective amount of a compound of formula (I)

wherein A¹, A², A³ and A⁴ are N, NX or CR⁴ wherein X is a lone pair orO, with the proviso that at most three of A¹, A², A³ and A⁴ are N or NX;R¹, R² are selected independently from one another from the groupconsisting of hydrogen, CN, NO₂, C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl,C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, wherein the carbon atoms of theaforementioned aliphatic and cycloaliphatic radicals may beunsubstituted or substituted with one or more R⁶; Si(R¹¹)₂R¹², OR⁷,S(O)_(m)R⁷, NR⁸R⁹, N═C(R⁶)₂, C(═O)R⁶, C(═S)R⁶, C(═NR⁸)R⁶ and a 3-, 4-,5-, 6- or 7-membered heterocyclic ring, wherein said heterocyclic ringis saturated or partially saturated, comprises 1, 2 or 3 heteroatomsselected from the group consisting of oxygen, nitrogen and sulfur,wherein the nitrogen and/or the sulfur atom(s) may be oxidized, isunsubstituted or substituted with one to five R¹⁰, and wherein one ortwo CH₂ groups in said heterocyclic ring may be replaced by one or twoC═O groups; R³ is selected from the group consisting of hydrogen,halogen, cyano, azido, nitro, SCN, SF₅, C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl,C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, wherein the carbon atoms of theaforementioned aliphatic and cycloaliphatic radicals may beunsubstituted or substituted with one or more R⁶; Si(R¹¹)₂R¹², OR⁷,S(O)_(m)R⁷, N(R⁸)R⁹, N═C(R⁶)₂, C(═O)R⁶, C(═S)R⁶, C(═NR⁸)R⁶, phenyl whichmay be substituted with 1, 2, 3, 4 or 5 radicals R¹⁰; and a 3-, 4-, 5-,6- or 7-membered heterocyclic ring, wherein said heterocyclic ring issaturated or partially saturated, comprises 1, 2 or 3 heteroatoms orheteroatom groups selected from the group consisting of N, O, S, NO, SOand SO₂, is unsubstituted or substituted with one to five radicals R¹⁰,and wherein one or two CH₂ groups in said heterocyclic ring may bereplaced by one or two C═O groups; each R⁴ is selected independentlyfrom the group consisting of hydrogen, halogen, cyano, azido, nitro,SCN, SF₅, C₃-C₈-cycloalkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, wherein thecarbon atoms of the aforementioned aliphatic and cycloaliphatic radicalsmay be unsubstituted or substituted with one or more R⁶; Si(R¹¹)₂R¹²,OR⁷, S(O)_(m)R⁷, N(R⁸)R⁹, N═C(R⁶)₂, C(═O)R⁶, C(═S)R⁶, C(═NR⁸)R⁶,C(═O)N(R⁸)R⁹, C(═S)N(R⁸)R⁹, phenyl which may be substituted with 1, 2,3, 4 or 5 radicals R¹⁰; and a 3-, 4-, 5-, 6- or 7-membered heterocyclicring, wherein said heterocyclic ring is saturated or partiallyunsaturated or aromatic, comprises 1, 2 or 3 heteroatoms or heteroatomgroups selected from the group consisting of N, O, S, NO, SO and SO₂, isunsubstituted or substituted with one to five radicals R¹⁰, and whereinone or two CH₂ groups in said saturated or partially saturated rings maybe replaced by one or two C═O groups; or two radicals R⁴ bound onadjacent carbon atoms together form a group selected from the groupconsisting of —CH₂CH₂CH₂CH₂—, —CH═CH—CH═CH—, —N═CH—CH═CH—, —CH═N—CH═CH—,—N═CH—N═CH—, —OCH₂CH₂CH₂—, —OCH═CHCH₂—, —CH₂OCH₂CH₂—, —OCH₂CH₂O—,—OCH₂OCH₂—, —CH₂CH₂CH₂—, —CH═CHCH₂—, —CH₂CH₂O—, —CH═CHO—, —CH₂OCH₂—,—CH₂C(═O)O—, —C(═O)OCH₂—, —O(CH₂)O—, —SCH₂CH₂CH₂—, —SCH═CHCH₂—,—CH₂SCH₂CH₂—, —SCH₂CH₂S—, —SCH₂SCH₂—, —CH₂CH₂S—, —CH═CHS—, —CH₂SCH₂—,—CH₂C(═S)S—, —C(═S)SCH₂—, —S(CH₂)S—, —CH₂CH₂NR⁸—, —CH₂CH═N—,—CH═CH—NR⁸—, —OCH═N— and —SCH═N—, wherein in each of the above group,one to five hydrogen atoms independently of each other may be replacedby one to five substituents selected from the group consisting ofhalogen, methyl, halomethyl, hydroxyl, methoxy and halomethoxy, or oneor two CH₂ groups of the above groups may be replaced by one or two C═Ogroups; R^(5a) is selected from the group consisting of hydrogen,halogen, cyano, azido, nitro, SCN, SF₅, C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl,C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, wherein the carbon atoms of theaforementioned aliphatic and cycloaliphatic radicals may beunsubstituted or substituted with one or more R⁶; Si(R¹¹)₂R¹², OR⁷,S(O)_(m)R⁷, N(R⁸)R⁹, N═C(R⁶)₂, C(═O)R⁶, C(═S)R⁶, C(═NR⁸)R⁶, phenyl whichmay be substituted with 1, 2, 3, 4 or 5 radicals R¹⁰; and a 3-, 4-, 5-,6- or 7-membered heterocyclic ring, wherein said heterocyclic ring issaturated or partially unsaturated or aromatic, comprises 1, 2 or 3heteroatoms or heteroatom groups selected from the group consisting ofN, O, S, NO, SO and SO₂, is unsubstituted or substituted with one tofive radicals R¹⁰, and wherein one or two CH₂ groups in said saturatedor partially saturated rings may be replaced by one or two C═O groups;or R^(5a) may form together with the adjacent carbon atom R^(5b) a 5- or6-membered ring which is at least substituted with one halogen; R^(5b)is selected from the group consisting of C₁-C₆-alkyl, C₃-C₆-cycloalkyl,C₁-C₆-alkoxy and C₁-C₆-cycloalkoxy, wherein each mentioned radical issubstituted with at least one halogen, may be further partially or fullyhalogenated, and may be substituted with one to five radicals R⁶; orR^(5b) may form together with the adjacent carbon atom R^(5c) or R^(5a)a 5- or 6-membered ring which is substituted with at least one halogen;R^(5c) is selected from the group consisting of hydrogen, halogen,cyano, azido, nitro, SCN, SF₅, C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl,C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, wherein the carbon atoms of theaforementioned aliphatic and cycloaliphatic radicals may beunsubstituted or substituted with one or more R⁶; Si(R¹¹)₂R¹², OR⁷,S(O)_(m)R⁷, N(R⁸)R⁹, N═C(R⁶)₂, C(═O)OR⁷, C(═S)OR⁷, C(═NR⁸)R⁶,C(═O)N(R⁸)R⁹, C(═S)N(R⁸)R⁹, phenyl which may be substituted with 1, 2,3, 4 or 5 radicals R¹⁰; and a 3-, 4-, 5-, 6- or 7-membered heterocyclicring, wherein said heterocyclic ring is saturated, partially unsaturatedor aromatic, comprises 1, 2 or 3 heteroatoms or heteroatom groupsselected from the group consisting of N, O, S, NO, SO and SO₂, isunsubstituted or substituted with one to five radicals R¹⁰, and whereinone or two CH₂ groups in said saturated or partially saturated rings maybe replaced by one or two C═O groups; or R^(sc) may form together withthe adjacent carbon atom R^(5b) or R^(5d) a 5- or 6-membered ring whichis substituted with at least one halogen in case of R^(5b) beinginvolved; R^(5d) is selected from the group consisting of hydrogen,halogen, cyano, azido, nitro, SCN, SF₅, C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl,C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, wherein the carbon atoms of theaforementioned aliphatic and cycloaliphatic radicals may beunsubstituted or substituted with one or more R⁶; Si(R¹¹)₂R¹², OR⁷,S(O)_(m)R⁷, S(O)_(m)N(R⁸)R⁹, N(R⁸)R⁹, N═C(R⁶)₂, C(═O)R⁶, C(═S)R⁶,C(═NR⁸)R⁶, phenyl which may be substituted with 1, 2, 3, 4 or 5 radicalsR¹⁰; and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring, wherein saidheterocyclic ring is saturated, partially unsaturated or aromatic,comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from thegroup consisting of N, O, S, NO, SO and SO₂, is unsubstituted orsubstituted with one to five radicals R¹⁰, and wherein one or two CH₂groups in said saturated or partially saturated rings may be replaced byone or two C═O groups; or R^(5d) may form together with the adjacentcarbon atom R^(5c) or with R¹ or R² a 5- or 6-membered ring; R⁶ isselected independently from the group consisting of hydrogen, halogen,cyano, azido, nitro, SCN, SF₅, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl,C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, wherein the carbon atom of the aforementioned aliphaticand cycloaliphatic radicals may be substituted with one or more R^(c);Si(R¹¹)₂R¹², OR^(o), O(CO)R^(c), O(CS)R^(c), S(O)_(m)R^(o),S(O)_(m)N(R^(n))₂, S(CO)R^(c), S(CS)R^(c), S(C═NR^(n))R^(c), N(R^(n))₂,N(R^(n))C(═O)R^(c), N(R^(n))C(═S)R^(c), NS(O)_(m)R^(o), N═C(R^(c))₂,C(═O)R^(c), C(═S)R^(c), C(═NR^(n))R^(c), C(═O)N(R^(n))₂, C(═S)N(R^(n))₂,phenyl which may be substituted with 1, 2, 3, 4 or 5 radicals R¹⁰; and a3-, 4-, 5-, 6- or 7-membered heterocyclic ring, wherein saidheterocyclic ring is saturated, partially unsaturated or aromatic,comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from thegroup consisting of N, O, S, NO, SO and SO₂, is unsubstituted orsubstituted with one to five radicals R¹⁰, and wherein one or two CH₂groups in said saturated or partially saturated rings may be replaced byone or two C═O groups; or two vicinally bound radicals R⁶ together forma group selected from ═C(R^(c))₂, ═S(O)_(m)R^(o), ═S(O)_(m)N(R^(n))₂,═NR^(n) and ═NN(R^(n))₂; R⁷ is selected independently from the groupconsisting of hydrogen, cyano, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl,C₃-C₈-cycloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein the carbon atomof the aforementioned aliphatic and cycloaliphatic radicals may besubstituted with one or more R^(c); Si(R¹¹)₂R¹², OR^(o), O(CO)R^(c),O(CS)R^(c), S(O)_(m)R^(o), S(O)_(m)N(R^(n))₂, S(CO)R^(c), S(CS)R^(c),S(C═NR^(n))R^(c), N(R^(n))₂, N(R^(n))C(═O)R^(c), N(R^(n))C(═S)R^(c),NS(O)_(m)R^(o), N═C(R^(c))₂, C(═O)R^(c), C(═S)R^(c), C(═NR^(n))R^(c),C(═O)N(R^(n))₂, C(═S)N(R^(n))₂, phenyl which may be substituted with 1,2, 3, 4 or 5 radicals R¹⁰; and a 3-, 4-, 5-, 6- or 7-memberedheterocyclic ring, wherein said heterocyclic ring is saturated,partially unsaturated or aromatic, comprises 1, 2 or 3 heteroatoms orheteroatom groups selected from the group consisting of N, O, S, NO, SOand SO₂, is unsubstituted or substituted with one to five radicals R¹⁰,and wherein one or two CH₂ groups in said saturated or partiallysaturated rings may be replaced by one or two C═O groups; with theproviso that R⁷ is not C₁-C₆-alkoxy or C₁-C₆-haloalkoxy if it is boundto an oxygen atom; R⁸, R⁹ are selected independently from one anotherand independently of each occurrence from the group consisting ofhydrogen, CN, NO₂, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio,C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, C₃-C₈-cycloalkyl,C₃-C₈-cycloalkyl-C₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein thecarbon atom of the aforementioned aliphatic and cycloaliphatic radicalsmay be substituted with one or more R^(c); Si(R¹¹)₂R¹², OR^(o),O(CO)R^(c), O(CS)R^(c), S(O)_(m)R^(o), S(O)_(m)N(R^(n))₂, S(CO)R^(c),S(CS)R^(c), S(C═NR^(n))R^(c), N(R^(n))₂, N(R^(n))C(═O)R^(c),N(R^(n))C(═S)R^(c), NS(O)_(m)R^(o), N═C(R^(c))₂, C(═O)R^(c), C(═S)R^(c),C(═NR^(n))R^(c), C(═O)N(R^(n))₂, C(═S)N(R^(n))₂ phenyl which may besubstituted with 1, 2, 3, 4 or 5 radicals R¹⁰; and a 3-, 4-, 5-, 6- or7-membered heterocyclic ring, wherein said heterocyclic ring issaturated, partially unsaturated or aromatic, comprises 1, 2 or 3heteroatoms or heteroatom groups selected from the group consisting ofN, O, S, NO, SO and SO₂, is unsubstituted or substituted with one tofive radicals R¹⁰, and wherein one or two CH₂ groups in said saturatedor partially saturated rings may be replaced by one or two C═O groups;R¹⁰ is selected independently from the group consisting of halogen,cyano, azido, nitro, SCN, SF₅, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl,C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, wherein the carbon atom of the aforementioned aliphaticand cycloaliphatic radicals may be substituted with one or more R^(c);Si(R¹¹)₂R¹², OR^(o), O(CO)R^(c), O(CS)R^(c), S(O)_(m)R^(o),S(O)_(m)N(R^(n))₂, S(CO)R^(c), S(CS)R^(c), S(C═NR^(n))R^(c), N(R^(n))₂,N(R^(n))C(═O)R^(c), N(R^(n))C(═S)R^(c), NS(O)_(m)R^(o), N═C(R^(c))₂,C(═O)R^(c), C(═S)R^(c), C(═NR^(n))R^(c), C(═O)N(R^(n))₂, C(═S)N(R^(n))₂,phenyl which may be substituted with one to five radicals selectedindependently from halogen, cyano, nitro, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₆-alkoxy and C₁-C₆-haloalkoxy; and a 3-, 4-, 5-, 6- or 7-memberedheterocyclic ring, wherein said heterocyclic ring is saturated orunsaturated, comprises 1, 2 or 3 heteroatoms or heteroatom groupsselected from the group consisting of N, O, S, NO, SO and SO₂, isunsubstituted or substituted with one to five radicals selectedindependently from the group consisting of halogen, cyano, nitro,C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy; or tworadicals R¹⁰ bound on adjacent atoms together form a group selected from—CH₂CH₂CH₂CH₂—, —CH═CH—CH═CH—, —N═CH—CH═CH—, —CH═N—CH═CH—, —N═CH—N═CH—,—OCH₂CH₂CH₂—, —OCH═CHCH₂—, —CH₂OCH₂CH₂—, —OCH₂CH₂O—, —OCH₂OCH₂—,—CH₂CH₂CH₂—, —CH═CHCH₂—, —CH₂CH₂O—, —CH═CHO—, —CH₂OCH₂—, —CH₂C(═O)O—,—C(═O)OCH₂—, —O(CH₂)O—, —SCH₂CH₂CH₂—, —SCH═CHCH₂—, —CH₂SCH₂CH₂—,—SCH₂CH₂S—, —SCH₂SCH₂—, —CH₂CH₂S—, —CH═CHS—, —CH₂SCH₂—, —CH₂C(═S)S—,—C(═S)SCH₂—, —S(CH₂)S—, —CH₂CH₂NR⁸—, —CH₂CH═N—, —CH═CH—NR⁸—, —OCH═N— and—SCH═N—, wherein in each of the above groups, one to five hydrogen atomsindependently of each other may be replaced by one to five substituentsselected from the group consisting of halogen, methyl, halomethyl,hydroxyl, methoxy and halomethoxy, or one or two or more CH₂ groups ofthe above groups may be replaced by one or two C═O groups; R¹¹, R¹² areselected independently of each other and independently of eachoccurrence from the group consisting of C₁-C₄-alkyl, C₃-C₆-cycloalkyl,C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl and benzyl; R^(c) is selectedindependently from the group consisting of hydrogen, halogen, cyano,azido, nitro, SCN, SF₅, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,C₁-C₆-haloalkylsulfonyl, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl,C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,C₂-C₆-haloalkynyl, phenyl, and a 3-, 4-, 5-, 6- or 7-memberedheterocyclic ring, wherein said heterocyclic ring is saturated,partially unsaturated or aromatic, comprises 1, 2 or 3 heteroatoms orheteroatom groups selected from CO, N, O, S, NO, SO and SO₂, isunsubstituted or substituted with one to five radicals, which areselected independently of each other from halogen, cyano, nitro,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; R^(o)is selected independently from the group consisting of hydrogen, cyano,C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl,C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl,C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl, C₃-C₈-halocycloalkyl,C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl,phenyl, and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring, whereinsaid heterocyclic ring is saturated, partially unsaturated or aromatic,comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from CO,N, O, S, NO, SO and SO₂, is unsubstituted or substituted with one tofive radicals, which are selected independently of each other fromhalogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy andC₁-C₄-haloalkoxy; with the proviso that R^(o) is not C₁-C₆-alkoxy orC₁-C₆-haloalkoxy if it is bound to an oxygen atom; R^(o) is selectedindependently from the group consisting of hydrogen, CN, NO₂,C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl,C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl,C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl, C₃-C₈-halocycloalkyl,C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl,phenyl, and a 3-, 4-, 5-, 6- or 7-membered saturated heterocyclic ring,wherein said heterocyclic ring is saturated, partially unsaturated oraromatic, comprises 1, 2 or 3 heteroatoms or heteroatom groups selectedfrom CO, N, O, S, NO, SO and SO₂, is unsubstituted or substituted withone to five radicals, which are selected independently of each otherfrom halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxyand C₁-C₄-haloalkoxy; m is independently 0, 1 or 2; p is 0, 1, 2, 3 or4; or enantiomers or diastereoisomers thereof or their agriculturally orveterinarily acceptable salts; or a composition comprising the compound.26. The method according to claim 25, wherein R^(5b) is selected fromthe group consisting of C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy andC₁-C₆-cycloalkoxy, wherein each mentioned radical is at leastsubstituted with one halogen.
 27. The method according to claim 25,wherein R³ is selected from the group consisting of hydrogen, halogen,cyano, azido, nitro, SCN, SF₅, C₁-C₆-haloalkyl, C₃-C₆-halocycloalkyl,C₁-C₆-haloalkoxy, C₃-C₆-halocycloalkoxy, Si(R¹¹)₂R¹², OR⁷, S(O)_(m)R⁷,N(R⁸)R⁹, N═(R⁶)₂, C(═O)R⁶, C(═S)R⁶ and C(═NR⁸)R⁶.
 28. The methodaccording to claim 25, wherein R^(5b) is selected from the groupconsisting of C₁-C₆-haloalkyl and C₁-C₆-haloalkoxy; R³ is selected fromthe group consisting of hydrogen, halogen, CN, NO₂, C(═NR⁸)R⁶,C₁-C₆-haloalkyl, C₃-C₆-halocycloalkyl, C₁-C₆-haloalkoxy andC₃-C₆-halocycloalkoxy.
 29. The method according to claim 25, whereinR^(5b) is CF₃; R³ is halogen; A¹, A², A³ and A⁴ are CR⁴; R^(5c) andR^(5d) are independently from one another hydrogen, halogen, C₁-C₆-alkylor C₁-C₆-haloalkyl; R^(5a) and each R⁴ are independently from oneanother hydrogen, halogen, CN, NO₂, C₁-C₆-alkyl, C₃-C₆-cycloalkyl,C₁-C₆-alkoxy or C₁-C₆-cycloalkoxy.
 30. The method according to claim 25,wherein R^(5b) is CF₃; R³ is halogen; A¹, A², A³ and A⁴ are CR⁴; R^(5c)and R^(5d) are hydrogen; R^(5a) and each R⁴ are independently from oneanother hydrogen, halogen, C₁-C₆-alkyl, or C₁-C₆-haloalkyl.
 31. A methodfor combating invertebrate pests attack or infestation which methodcomprises treating the pests, their food supply, their habitat, theirbreeding ground, the plant, the plant propagation material, soil, area,material or environment in which the pests are growing or may grow, witha pesticidally effective amount of at least one compound of the formulaI as defined in claim 19 or a composition comprising it.
 32. Plantpropagation material treated with the compound of claim 19 or acomposition comprising the compound.
 33. Seeds treated with a compoundof claim 19 in an amount of from 0.1 g to 10 kg per 100 kg of seed. 34.A method for treating, controlling, preventing or protecting an animalfrom infestation or infection by invertebrate pests which comprisesbringing the animal in contact with a pesticidally effective amount ofat least one compound of the formula I as defined in claim
 19. 35. Acompound of formula (I)

wherein A¹, A², A³ and A⁴ are N, NX or CR⁴ wherein X is a lone pair orO, with the proviso that at most three of A¹, A², A³ and A⁴ are N or NX;R¹, R² are selected independently from one another from the groupconsisting of hydrogen, CN, NO₂, C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl,C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, wherein the carbon atoms of theaforementioned aliphatic and cycloaliphatic radicals may beunsubstituted or substituted with one or more R⁶; Si(R¹¹)₂R¹²,OS(O)_(m)R⁷, NR⁸R⁹, N═C(R⁶)₂, C(═O)R⁶, C(═S)R⁶, C(═NR⁸)R⁶ and a 3-, 4-,5-, 6- or 7-membered heterocyclic ring, wherein said heterocyclic ringis saturated or partially saturated, comprises 1, 2 or 3 heteroatomsselected from the group consisting of oxygen, nitrogen and sulfur,wherein the nitrogen and/or the sulfur atom(s) may be oxidized, isunsubstituted or substituted with one to five R¹⁰, and wherein one ortwo CH₂ groups in said heterocyclic ring may be replaced by one or twoC═O groups; R³ is selected from the group consisting of hydrogen,halogen, cyano, azido, nitro, SCN, SF₅, C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl,C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, wherein the carbon atoms of theaforementioned aliphatic and cycloaliphatic radicals may beunsubstituted or substituted with one or more R⁶; Si(R¹¹)₂R¹², OR⁷,S(O)_(m)R⁷, N(R⁸)R⁹, N═C(R⁶)₂, C(═O)R⁶, C(═S)R⁶, C(═NR⁸)R⁶, phenyl whichmay be substituted with 1, 2, 3, 4 or 5 radicals R¹⁰; and a 3-, 4-, 5-,6- or 7-membered heterocyclic ring, wherein said heterocyclic ring issaturated or partially saturated, comprises 1, 2 or 3 heteroatoms orheteroatom groups selected from the group consisting of N, O, S, NO, SOand SO₂, is unsubstituted or substituted with one to five radicals R¹⁰,and wherein one or two CH₂ groups in said heterocyclic ring may bereplaced by one or two C═O groups; each R⁴ is selected independentlyfrom the group consisting of hydrogen, halogen, cyano, azido, nitro,SCN, SF₅, C₃-C₈-cycloalkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, wherein thecarbon atoms of the aforementioned aliphatic and cycloaliphatic radicalsmay be unsubstituted or substituted with one or more R⁶; Si(R¹¹)₂R¹²,OR⁷, S(O)_(m)R⁷, N(R⁸)R⁹, N═C(R⁶)₂, C(═O)R⁶, C(═S)R⁶, C(═NR⁸)R⁶,C(═O)N(R⁸)R⁹, C(═S)N(R⁸)R⁹, phenyl which may be substituted with 1, 2,3, 4 or 5 radicals R¹⁰; and a 3-, 4-, 5-, 6- or 7-membered heterocyclicring, wherein said heterocyclic ring is saturated or partiallyunsaturated or aromatic, comprises 1, 2 or 3 heteroatoms or heteroatomgroups selected from the group consisting of N, O, S, NO, SO and SO₂, isunsubstituted or substituted with one to five radicals R¹⁰, and whereinone or two CH₂ groups in said saturated or partially saturated rings maybe replaced by one or two C═O groups; or two radicals R⁴ bound onadjacent carbon atoms together form a group selected from the groupconsisting of —CH₂CH₂CH₂CH₂—, —CH═CH—CH═CH—, —N═CH—CH═CH—, —CH═N—CH═CH—,—N═CH—N═CH—, —OCH₂CH₂CH₂—, —OCH═CHCH₂—, —CH₂OCH₂CH₂—, —OCH₂CH₂O—,—OCH₂OCH₂—, —CH₂CH₂CH₂—, —CH═CHCH₂—, —CH₂CH₂O—, —CH═CHO—, —CH₂OCH₂—,—CH₂C(═O)O—, —C(═O)OCH₂—, —O(CH₂)O—, —SCH₂CH₂CH₂—, —SCH═CHCH₂—,—CH₂SCH₂CH₂—, —SCH₂CH₂S—, —SCH₂SCH₂—, —CH₂CH₂S—, —CH═CHS—, —CH₂SCH₂—,—CH₂C(═S)S—, —C(═S)SCH₂—, —S(CH₂)S—, —CH₂CH₂NR⁸—, —CH₂CH═N—,—CH═CH—NR⁸—, —OCH═N— and —SCH═N—, wherein in each of the above group,one to five hydrogen atoms independently of each other may be replacedby one to five substituents selected from the group consisting ofhalogen, methyl, halomethyl, hydroxyl, methoxy and halomethoxy, or oneor two CH₂ groups of the above groups may be replaced by one or two C═Ogroups; R^(5a) is selected from the group consisting of hydrogen,halogen, cyano, azido, nitro, SCN, SF₅, C₃-C₈-cycloalkyl,C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, wherein the carbon atoms of theaforementioned aliphatic and cycloaliphatic radicals may beunsubstituted or substituted with one or more R⁶; Si(R¹¹)₂R¹², OR⁷,S(O)_(m)R⁷, N(R⁸)R⁹, N═C(R⁶)₂, C(═O)R⁶, C(═S)R⁶, C(═NR⁸)R⁶, phenyl whichmay be substituted with 1, 2, 3, 4 or 5 radicals R¹⁰; and a 3-, 4-, 5-,6- or 7-membered heterocyclic ring, wherein said heterocyclic ring issaturated or partially unsaturated or aromatic, comprises 1, 2 or 3heteroatoms or heteroatom groups selected from the group consisting ofN, O, S, NO, SO and SO₂, is unsubstituted or substituted with one tofive radicals R¹⁰, and wherein one or two CH₂ groups in said saturatedor partially saturated rings may be replaced by one or two C═O groups;or R^(5a) may form together with the adjacent carbon atom R^(5b) a 5- or6-membered ring which is at least substituted with one halogen; R^(5b)is selected from the group consisting of C₁-C₆-alkyl, C₃-C₆-cycloalkyl,C₁-C₆-alkoxy and C₁-C₆-cycloalkoxy, wherein each mentioned radical issubstituted with at least one halogen, may be further partially or fullyhalogenated, and may be substituted with one to five radicals R⁶; orR^(5b) may form together with the adjacent carbon atom R^(5c) or R^(5a)a 5- or 6-membered ring which is substituted with at least one halogen;R^(5c) is selected from the group consisting of hydrogen, halogen,cyano, azido, nitro, SCN, SF₅, C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl,C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, wherein the carbon atoms of theaforementioned aliphatic and cycloaliphatic radicals may beunsubstituted or substituted with one or more R⁶; Si(R¹¹)₂R¹², OR⁷,S(O)_(m)R⁷, N(R⁸)R⁹, N═C(R⁶)₂, C(═O)OR⁷, C(═S)OR⁷, C(═NR⁸)R⁶,C(═O)N(R⁸)R⁹, C(═S)N(R⁸)R⁹, phenyl which may be substituted with 1, 2,3, 4 or 5 radicals R¹⁰; and a 3-, 4-, 5-, 6- or 7-membered heterocyclicring, wherein said heterocyclic ring is saturated, partially unsaturatedor aromatic, comprises 1, 2 or 3 heteroatoms or heteroatom groupsselected from the group consisting of N, O, S, NO, SO and SO₂, isunsubstituted or substituted with one to five radicals R¹⁰, and whereinone or two CH₂ groups in said saturated or partially saturated rings maybe replaced by one or two C═O groups; or R^(5c) may form together withthe adjacent carbon atom R^(5b) or R^(5d) a 5- or 6-membered ring whichis substituted with at least one halogen in case of R^(5b) beinginvolved; R^(5d) is selected from the group consisting of hydrogen,halogen, cyano, azido, nitro, SCN, SF₅, C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl,C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, wherein the carbon atoms of theaforementioned aliphatic and cycloaliphatic radicals may beunsubstituted or substituted with one or more R⁶; Si(R¹¹)₂R¹²,S(O)_(m)R⁷, S(O)_(m)N(R⁸)R⁹, N(R⁸)R⁹, N═C(R⁶)₂, C(═O)R⁶, C(═S)R⁶,C(═NR⁸)R⁶, phenyl which may be substituted with 1, 2, 3, 4 or 5 radicalsR¹⁰; and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring, wherein saidheterocyclic ring is saturated, partially unsaturated or aromatic,comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from thegroup consisting of N, O, S, NO, SO and SO₂, is unsubstituted orsubstituted with one to five radicals R¹⁰, and wherein one or two CH₂groups in said saturated or partially saturated rings may be replaced byone or two C═O groups; or R^(5d) may form together with the adjacentcarbon atom R^(5c) or with R¹ or R² a 5- or 6-membered ring; R⁶ isselected independently from the group consisting of hydrogen, halogen,cyano, azido, nitro, SCN, SF₅, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl,C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, wherein the carbon atom of the aforementioned aliphaticand cycloaliphatic radicals may be substituted with one or more R^(c);Si(R¹¹)₂R¹², OR^(o), O(CO)R^(c), O(CS)R^(c), S(O)_(m)R^(o),S(O)_(m)N(R^(n))₂, S(CO)R^(c), S(CS)R^(c), S(C═NR^(n))R^(c), N(R^(n))₂,N(R^(n))C(═O)R^(c), N(R^(n))C(═S)R^(c), NS(O)_(m)R^(o), N═C(R^(c))₂,C(═O)R^(c), C(═S)R^(c), C(═NR^(n))R^(c), C(═O)N(R^(n))₂, C(═S)N(R^(n))₂,phenyl which may be substituted with 1, 2, 3, 4 or 5 radicals R¹⁰; and a3-, 4-, 5-, 6- or 7-membered heterocyclic ring, wherein saidheterocyclic ring is saturated, partially unsaturated or aromatic,comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from thegroup consisting of N, O, S, NO, SO and SO₂, is unsubstituted orsubstituted with one to five radicals R¹⁰, and wherein one or two CH₂groups in said saturated or partially saturated rings may be replaced byone or two C═O groups; or two vicinally bound radicals R⁶ together forma group selected from ═C(R^(c))₂, ═S(O)_(m)R^(o), ═S(O)_(m)N(R^(n))₂,═NR^(n) and ═NN(R^(n))₂; R⁷ is selected independently from the groupconsisting of hydrogen, cyano, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl,C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, wherein the carbon atom of the aforementioned aliphaticand cycloaliphatic radicals may be substituted with one or more R^(c);Si(R¹¹)₂R¹², OR^(o), O(CO)R^(c), O(CS)R^(c), S(O)_(m)R^(o),S(O)_(m)N(R^(n))₂, S(CO)R^(c), S(CS)R^(c), S(C═NR^(n))R^(c), N(R^(n))₂,N(R^(n))C(═O)R^(c), N(R^(n))C(═S)R^(c), NS(O)_(m)R^(o), N═C(R^(c))₂,C(═O)R^(c), C(═S)R^(c), C(═NR^(n))R^(c), C(═O)N(R^(n))₂, C(═S)N(R^(n))₂,phenyl which may be substituted with 1, 2, 3, 4 or 5 radicals R¹⁰; and a3-, 4-, 5-, 6- or 7-membered heterocyclic ring, wherein saidheterocyclic ring is saturated, partially unsaturated or aromatic,comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from thegroup consisting of N, O, S, NO, SO and SO₂, is unsubstituted orsubstituted with one to five radicals R¹⁰, and wherein one or two CH₂groups in said saturated or partially saturated rings may be replaced byone or two C═O groups; with the proviso that R⁷ is not C₁-C₆-alkoxy orC₁-C₆-haloalkoxy if it is bound to an oxygen atom; R⁸, R⁹ are selectedindependently from one another and independently of each occurrence fromthe group consisting of hydrogen, CN, NO₂, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl,C₃-C₈-cycloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein the carbon atomof the aforementioned aliphatic and cycloaliphatic radicals may besubstituted with one or more R^(c); Si(R¹¹)₂R¹², OR^(o), O(CO)R^(c),O(CS)R^(c), S(O)_(m)R^(o), S(O)_(m)N(R^(n))₂, S(CO)R^(c), S(CS)R^(c),S(C═NR^(n))R^(c), N(R^(n))₂, N(R^(n))C(═O)R^(c), N(R^(n))C(═S)R^(c),NS(O)_(m)R^(o), N═C(R^(c))₂, C(═O)R^(c), C(═S)R^(c), C(═NR^(n))R^(c),C(═O)N(R^(n))₂, C(═S)N(R^(n))₂ phenyl which may be substituted with 1,2, 3, 4 or 5 radicals R¹⁰; and a 3-, 4-, 5-, 6- or 7-memberedheterocyclic ring, wherein said heterocyclic ring is saturated,partially unsaturated or aromatic, comprises 1, 2 or 3 heteroatoms orheteroatom groups selected from the group consisting of N, O, S, NO, SOand SO₂, is unsubstituted or substituted with one to five radicals R¹⁰,and wherein one or two CH₂ groups in said saturated or partiallysaturated rings may be replaced by one or two C═O groups; R¹⁰ isselected independently from the group consisting of halogen, cyano,azido, nitro, SCN, SF₅, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio,C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, C₃-C₈-cycloalkyl,C₃-C₈-cycloalkyl-C₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein thecarbon atom of the aforementioned aliphatic and cycloaliphatic radicalsmay be substituted with one or more R^(c); Si(R¹¹)₂R¹², OR^(o),O(CO)R^(c), O(CS)R^(c), S(O)_(m)R^(o), S(O)_(m)N(R^(n))₂, S(CO)R^(c),S(CS)R^(c), S(C═NR^(n))R^(c), N(R^(n))₂, N(R^(n))C(═O)R^(c),N(R^(n))C(═S)R^(c), NS(O)_(m)R^(o), N═C(R^(c))₂, C(═O)R^(c), C(═S)R^(c),C(═NR^(n))R^(c), C(═O)N(R^(n))₂, C(═S)N(R^(n))₂, phenyl which may besubstituted with one to five radicals selected independently fromhalogen, cyano, nitro, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy andC₁-C₆-haloalkoxy; and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,wherein said heterocyclic ring is saturated or unsaturated, comprises 1,2 or 3 heteroatoms or heteroatom groups selected from the groupconsisting of N, O, S, NO, SO and SO₂, is unsubstituted or substitutedwith one to five radicals selected independently from the groupconsisting of halogen, cyano, nitro, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₆-alkoxy and C₁-C₆-haloalkoxy; or two radicals R¹⁰ bound on adjacentatoms together form a group selected from —CH₂CH₂CH₂CH₂—, —CH═CH—CH═CH—,—N═CH—CH═CH—, —CH═N—CH═CH—, —N═CH—N═CH—, —OCH₂CH₂CH₂—, —OCH═CHCH₂—,—CH₂OCH₂CH₂—, —OCH₂CH₂O—, —OCH₂OCH₂—, —CH₂CH₂CH₂—, —CH═CHCH₂—,—CH₂CH₂O—, —CH═CHO—, —CH₂OCH₂—, —CH₂C(═O)O—, —C(═O)OCH₂—, —O(CH₂)O—,—SCH₂CH₂CH₂—, —SCH═CHCH₂—, —CH₂SCH₂CH₂—, —SCH₂CH₂S—, —SCH₂SCH₂—,—CH₂CH₂S—, —CH═CHS—, —CH₂SCH₂—, —CH₂C(═S)S—, —C(═S)SCH₂—, —S(CH₂)S—,—CH₂CH₂NR⁸—, —CH₂CH═N—, —CH═CH—NR⁸—, —OCH═N— and —SCH═N—, wherein ineach of the above groups, one to five hydrogen atoms independently ofeach other may be replaced by one to five substituents selected from thegroup consisting of halogen, methyl, halomethyl, hydroxyl, methoxy andhalomethoxy, or one or two or more CH₂ groups of the above groups may bereplaced by one or two C═O groups; R¹¹, R¹² are selected independentlyof each other and independently of each occurrence from the groupconsisting of C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,phenyl and benzyl; R^(c) is selected independently from the groupconsisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF₅,C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl,C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl,C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl, C₃-C₈-halocycloalkyl,C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl,phenyl, and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring, whereinsaid heterocyclic ring is saturated, partially unsaturated or aromatic,comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from CO,N, O, S, NO, SO and SO₂, is unsubstituted or substituted with one tofive radicals, which are selected independently of each other fromhalogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy andC₁-C₄-haloalkoxy; R^(o) is selected independently from the groupconsisting of hydrogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,C₁-C₆-haloalkylsulfonyl, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl,C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,C₂-C₆-haloalkynyl, phenyl, and a 3-, 4-, 5-, 6- or 7-memberedheterocyclic ring, wherein said heterocyclic ring is saturated,partially unsaturated or aromatic, comprises 1, 2 or 3 heteroatoms orheteroatom groups selected from CO, N, O, S, NO, SO and SO₂, isunsubstituted or substituted with one to five radicals, which areselected independently of each other from halogen, cyano, nitro,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; withthe proviso that R^(o) is not C₁-C₆-alkoxy or C₁-C₆-haloalkoxy if it isbound to an oxygen atom; R^(n) is selected independently from the groupconsisting of hydrogen, CN, NO₂, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,C₁-C₆-haloalkylsulfonyl, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl,C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,C₂-C₆-haloalkynyl, phenyl, and a 3-, 4-, 5-, 6- or 7-membered saturatedheterocyclic ring, wherein said heterocyclic ring is saturated,partially unsaturated or aromatic, comprises 1, 2 or 3 heteroatoms orheteroatom groups selected from CO, N, O, S, NO, SO and SO₂, isunsubstituted or substituted with one to five radicals, which areselected independently of each other from halogen, cyano, nitro,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; m isindependently 0, 1 or 2; p is 0, 1, 2, 3 or 4; or enantiomers ordiastereoisomers thereof or their agriculturally or veterinarilyacceptable salts, with the exception of2-[4-[2-aminoethyamino]-7-trifluoromethyl-quinazolin-2-yl]-phenol, andthe salts and N-oxides thereof.
 36. The compound of claim 31, whereinR^(5b) is selected from the group consisting of C₁-C₆-alkyl,C₃-C₆-cycloalkyl, C₁-C₆-alkoxy and C₁-C₆-cycloalkoxy, wherein eachmentioned radical is at least substituted with one halogen.
 37. Thecompound of claim 31, wherein R³ is selected from the group consistingof hydrogen, halogen, cyano, azido, nitro, SCN, SF₅, C₁-C₆-haloalkyl,C₃-C₆-halocycloalkyl, C₁-C₆-haloalkoxy, C₃-C₆-halocycloalkoxy,Si(R¹¹)₂R¹², OR⁷, S(O)_(m)R⁷, N(R⁸)R⁹, N═(R⁶)₂, C(═O)R⁶, C(═S)R⁶ andC(═NR⁸)R⁶.
 38. The compound of claim 31, wherein R^(5b) is selected fromthe group consisting of C₁-C₆-haloalkyl and C₁-C₆-haloalkoxy; R³ isselected from the group consisting of hydrogen, halogen, CN, NO₂,C(═NR⁸)R⁶, C₁-C₆-haloalkyl, C₃-C₆-halocycloalkyl, C₁-C₆-haloalkoxy andC₃-C₆-halocycloalkoxy.
 39. The compound of claim 31, wherein R^(5b) isCF₃; R³ is halogen; A¹, A², A³ and A⁴ are CR⁴; R^(5c) and R^(5d) areindependently from one another hydrogen, halogen, C₁-C₆-alkyl orC₁-C₆-haloalkyl; R^(5a) and each R⁴ are independently from one anotherhydrogen, halogen, CN, NO₂, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxyor C₁-C₆-cycloalkoxy.
 40. The compound of claim 31, wherein R^(5b) isCF₃; R³ is halogen; A¹, A², A³ and A⁴ are CR⁴; R^(5c) and R^(5d) arehydrogen; R^(5a) and each R⁴ are independently from one anotherhydrogen, halogen, C₁-C₆-alkyl, or C₁-C₆-haloalkyl.